6

MAKE THE GRADE

It had long since come to my attention that people of accomplishment rarely sat back and let things happen to them. They went out and happened to things.

—LEONARDO DA VINCI

When you raise your hand and step into the role of “the leader,” you are making the choice (whether you are conscious of it or not) to be responsible for the results of your team. After embedding himself with New Zealand’s All Blacks rugby team for a period of time, author James Kerr described to me the role of the leader as the person who “is responsible for the result, whatever that result is. And that sense of personal responsibility and ownership and accountability for that result—whichever way it goes: responsible if there’s a win, but also equally responsible if things don’t go to plan. Ownership and accountability and taking it on the chin, I think, is really fundamental. They’re all kind of embroiled in that same knot of team and connection and authentic accountability.”¹

Being “responsible for the result” may sound simple enough. Most clichés do, in fact, and being accountable for results is certainly a well-worn cliché in leadership circles. But just because something is a cliché doesn’t mean it ceases to be true. Yet there’s a lot more to it than simply saying, “I’m responsible,” and being the one who has to answer to others (a boss, a customer, a board, investors) for those results. Being accountable for your team’s performance is a part of team leadership, but so too is the accountability you owe to your team to do the things that will help them achieve those results. Taking the blame or accepting the reward is simple and straightforward, even if it’s not altogether easy. (If it was, blame-shifting and avoidance of accountability wouldn’t be such a widespread leadership problem.) Affecting the outcome of the collective work of an organization or team is something else entirely. This side of leadership is much harder and far more complex, which is why it is done well so rarely.

RESULTS MATTER

Early in my career, I met with an executive from another company who had shown interest in hiring me for a significant leadership role. During that interview, he said to me, “I look for people who have had success in multiple life categories. I want leaders who’ve shown that they have the skill, will, and desire to ‘figure it out,’ regardless of the situation.” Even though many years have passed since that meeting, I still remember his words with vivid clarity. I didn’t end up taking the job that was offered, but that interview impacted me in a permanent fashion, nonetheless.

Excellent leaders get results. If the coach loses too many games, he gets fired. Regardless of the sport, this is a certainty. Likewise, in business: a leader who fails to produce results will soon find herself no longer leading her team. While I firmly believe in the virtue of focusing on the process to get there, it is vital that your record reflects a habit of actually “getting there.”

Why? Organizations need to progress. They need to achieve revenue targets, to complete projects on time and within budget, and to create positive momentum moving forward. The responsibility for making that happen lies with the leader. Showing that you’ve done that in the past was likely key to earning that big promotion, and doing it now as the new leader is vital to keeping your current role and to setting yourself up for the next growth opportunity. How do you do that? In a nutshell: by understanding the role you play, understanding the tools you have at your disposal to help you, learning from your and others’ experiences, and making the adjustments necessary to drive improvements.

“YOU HAVE TO DO ALL THREE”

When I landed the promotion that made me a manager for the first time, my initial plan was to stick to my natural strengths. I remember talking it over with my dad and telling him, “I’m more of an inspirational leader. I’ll share vision and inspire the team to exceed our goals. I’m not really a numbers guy. I’ll get someone else to help me with that.” My dad didn’t hesitate to stop that train of thought right in its tracks. “Don’t ever say or think that again,” he said. “You are running the team. You are now a leader. You must become a ‘numbers guy’ and continue to inspire. You need to lead, manage, and coach. To be excellent, you have to do all three.”

Looking back at my mindset is a bit embarrassing, frankly. I somehow got it into my head that I could be an excellent leader while only doing part of the job. Time proved my dad right, of course. Once I took on the responsibility of answering for the results of my team, I knew why: I couldn’t fairly handle that responsibility if I wasn’t willing to wear all three hats required of the role.

You may be asking yourself, “What’s the difference between leading, managing, and coaching anyway? Is it just semantics?” There are many who say it is, including leaders I respect and admire like Tom Peters: “Leadership entails enormous responsibility. Management entails enormous responsibility. But my statement is silly, because there is no difference between the two.”² Peters’s expertise and view notwithstanding, I have found it helpful throughout my career to think of these three words as distinct functions, which overlap and intersect within the single role of being responsible for the performance of others, regardless of whether you call yourself a “leader,” a “manager,” or a “coach.” And so, with apologies to Tom, that’s how I will discuss them in this chapter.

Leading

“Leadership is at its best when the vision is strategic, the voice persuasive, and the results are tangible,” writes Michael Useem.³ The act of leading is about providing purpose, direction, and inspiration to the group. It presents a vision, sees the big picture, and devises a strategy to accomplish the mission at hand. In focusing on the communication of goals, building teams and coalitions, and seeking commitment from its members, the effect of leading on those members should be one of inspiration and empowerment. From Tom Peters:

I believe that effective leadership—in a six-person accounting office, an elementary school, a computer factory, or a nation—is largely a function of the chief’s vitality, willingness to empower others, and skill at exciting individuals about their own and their group’s purposes.

In business, the supreme strategist, who can dissect markets the way a chess master can evaluate his next five moves, is a precious commodity. But the chess master need only out-think his opponent. Once he decides to make a move, physically shifting the piece follows automatically.

Not so for the leader of any organization. His or her rooks, knights, and pawns must be inspired—and then inspired all over again tomorrow—if world-class quality and continuous improvement are to be the everyday result.⁴

To lead well means to have what Robert Greene calls “a third eye”—a way of guiding you toward the larger picture while avoiding getting trapped in the hell of tactics. A great leader has an overriding sense of where she is taking the team at the macro level. “Most of us in life are tacticians, not strategists, writes Greene in his book, The 33 Strategies of War.⁵ “We become so enmeshed in the conflicts we face that we can think only of how to get what we want in the battle we are currently facing. To think strategically is difficult and unnatural. You may imagine you are being strategic, but in all likelihood, you are merely being tactical.”⁶ Strategists think beyond a single battle or even a series of battles. They are focused on the playbook of the long game, in which they expect to survive multiple defeats and still push forward to victory. They don’t fight just because the enemy army is present—they only fight when the time and location is right. Even then, they ask questions like “Is it possible to gain victory without fighting this battle?”

To have the power that only strategy can bring, you must be able to elevate yourself above the battlefield, to focus on your long-term objectives, to craft an entire campaign, to get out of the reactive mode that so many battles in life lock you into. Keeping your overall goals in mind, it becomes much easier to decide when to fight and when to walk away.⁷

One of the biggest changes a manager goes through as they make the transition from individual contributor to leader is the necessary shift in mindset to thinking about the business from this higher-level perspective. As an individual contributor, you often only need to think of your goals, your actions, your work, your objective, at a singular level. When you get promoted, that all changes. You start thinking about company objectives, company mission, vision, and plans. And if you want to continue to progress, it’s wise to start thinking about this as soon as possible. I did not learn this right away, but wish I had.

In order to lead like a strategic visionary, you must start by thinking like one. That means thinking through a progression of lenses, from the most high-level and general to ground-level and specific: from mission to vision to strategy to tactics.

This is our path to being a more strategic leader. Let’s break it down.

Mission. Why do we do what we do? Why does our company exist? Why does THIS team (the one I am now leading) exist?

Vision. Where we are heading? It is the ultimate destination that connects the mission to our product, service, or goal, and therefore is necessarily aspirational in nature.

Strategy. This is the planning framework for how we will do the work of getting to the destination identified in our vision.

Tactics. The details of what must be done at an individual level to execute the plan. This is precisely what you are to do. The job function in specific detail. Given that, it should be collaborative, and the leader should empower the team in the planning process. And it must be vividly clear when rolled out. Ensure all questions are answered and the team is aligned and knows the plan. All tactics should be measurable and have ownership at the individual level.

• • • • •

A good system for thinking strategically and keeping that focus is to list your “Big 5” annual priorities. With such a list, you are positioned to plan how you will spend your time and effort working toward accomplishing these five. Here is an example of what that looks like, from my days leading a sales team:

1.   Supporting employees and customers. Striving to be ever more intentional about taking care of the most important people to your team’s success (your employees) and the second-most important people (your customers). Good intentions don’t turn out to be much in the end unless and until they are channeled through well-designed systems aimed at operationalizing those noble ideas. Building those systems will take work.

2.   Maintaining the optimal level and mix of talent of your team. This is all about recruiting, hiring, training, and coaching.

3.   Managing the metrics that matter. What are the behaviors that truly lead to long-term sustained excellence on your team? Because “what gets measured gets managed,” it’s critical that you know what matters most, have a way of measuring that, and then hold your team accountable for those results.

4.   Driving new account acquisition. In business as in life, to live is to grow, and to grow is to live. Every company needs to continually acquire new customers if they are to grow.

5.   Keeping your current customers happy. Counterintuitively, some of the biggest opportunities for growth lie with the happy clients you already have. Knowing how to identify those opportunities and convert them is vital. A bonus that comes from this key strategic focus are the insights you develop from regular contact with your actual customers (rather than just the reports of what your customers are doing). Whether or not you work in sales, a portion of your time should be spent on the front lines with the people who buy and use your product. Hear what they say about it: why they like it, what could be improved. Get their actual quotes. Feel their happiness and pain from what you offer. Gaining an understanding of how they actually speak will make you a better leader and better champion for your company. When giving a presentation, it’s much more persuasive and impactful to use real quotes from real customers than to display a bunch of numbers on a screen. Learn their stories, and tell their stories. Get in the field and learn from firsthand experience.

Managing

Great management is figuring out how to work within the current constraints of the system you are in. It is the administration and stewardship of resources. It is because those resources are always limited—always—that the act of managing is even necessary. If time and money were truly of no consequence, then the very idea of a manager becomes irrelevant, for there are no decisions that need to be made: unlimited resources can be thrown at every project, and the work can take as long as it requires without consequence. In your new role as a manager, you will run into the hard limits of your resources—whether time, budget, or manpower—sooner than you would like. When you do, take heart. It is those limitations that make your new job a necessary one.

As a new manager, I was given a salary and variable compensation budget to work within (for the people I was to hire and work to retain). There was no negotiation, and I had no ability to request more money. That was what was budgeted and if the “superstar” candidate I desperately wanted demanded more money, I was out of luck. I had to find a way to make it work within those constraints. As a mid-level manager, this is part of the deal.

The same is true of the goals you will be accountable for leading your team to hit. Whether your team is charged with meeting targets on revenue growth, customer acquisition, product deployment, customer service success, or project management timelines, the dynamic will almost always feel the same: the constraints of aggressive goals, oftentimes set and dictated without your input.

When it came to the sales goals set annually for my team, if I felt they were unreasonable (an entirely common complaint among sales managers, regardless of industry), it didn’t really matter. Those were the goals, and my job was to get our team to meet them, regardless of how unreasonable I felt they were. I learned to apply the advice my mom always gave me at times like this: “Don’t worry about things that are out of your control. Only concern yourself with things where you can make an impact.”

Resource constraints demand creativity. When you don’t have the luxury of throwing more money or people at a problem, you must be able to step back, identify what it is you’re trying to accomplish, and find a different way to do it. I would regularly request extra funds from various parts of the business for a “special contest” or anything to help inspire my team and get them excited. I worked in a multibillion-dollar business in which my team (in the grand scheme of things) represented a tiny fraction. I felt it was my job to seek out and find ways to show them love, compensate them with prizes, money, trophies, and great feedback when they worked hard and overachieved. But getting the extra money I asked for didn’t always happen. In those situations, I had to come up with other ways to help my team feel rewarded and appreciated for their great performance.

I had a regular practice of sending emails to the senior leaders above me with a request for them. I’d ask them to send a “great job!” email to a member of my team that said something like: “Hey Jameson, I heard from Ryan that you are crushing it. One hundred eighty-nine percent of plan in April?! Wow, congratulations and thank you for your hard work!” Sometimes, I would draft the email for the senior leader because I knew how busy they were, and the last thing they wanted was another item on their massive to-do list. Invariably, the senior leaders were all too willing to oblige, especially when I made it easy for them to do good and look good doing it. Not a bad tradeoff for the few seconds it takes to copy what I wrote into their email, put my team member’s email in the To: field, and hit send.

All of these little details are important, and they make a difference. All of us want to feel love and recognition when we’ve worked hard and done a great job. It is the manager’s responsibility to make sure they feel that love when they’ve earned it, and to figure out creative ways to make that happen when your resources are limited.

Another type of resource that a great manager must learn how to make use of is the organization itself, and the network of possible partners it contains. Building allies and consensus around ideas and initiatives with other leaders in the business is one of the key aspects of being a manager that you don’t think of as an individual contributor. Cultivating real relationships with other leaders who have nothing to do with your work, but may at some point in time is the necessary prep work for the task of leading through influence. You can’t just go to these people when you need something from them. Doing so risks creating the opposite of a virtuous cycle: if you start to become known as someone who only interacts with others when you want something from them, the chances of them agreeing to help go down. On the other hand, if you have previously invested the time and effort into building a real relationship with someone, then when you need their assistance or their backing on an initiative, it is much more likely to happen. Do the planting work of building connections ahead of time with no specific goal in sight, and you’ll be amazed at the generosity you will someday harvest when you most need it.

• • • • •

Managing limited resources is only one arena that requires the manager’s attention. Another ubiquitous, but ever true cliché, vying for the manager’s attention is “managing change.” As your competitive business market never stops changing, so, too, will the ways your company conducts its affairs internally. As the leader of your team, your people will either experience these never-ending changes for the better or for the worse, depending on how you navigate them. When done well, how you manage change can serve as the steady bow of your team’s ship, helping it cut through the turbulent waves of change while still staying on your prescribed course.

The primary reason change is met with resistance is uncertainty. No one likes uncertainty. If people lack confidence that their leaders really have a clear plan for where they’re going, the chances that those changes are going to be implemented well and yield positive results are slim. Marcus Buckingham, author of First, Break All the Rules, says that it is this alleviation of uncertainty that makes leaders worth following: “You follow someone because they give you confidence in the future. ‘I want to hitch my wagon to you.’ The future can be scary and uncertain. A great leader finds a way of making the world less scary and bringing a level of certainty to a situation.”⁸

One way to help your team navigate change successfully is to help them focus on what isn’t changing. Many leaders try to implement change by highlighting the problems of the current state and contrasting that with the expected benefits of the new initiative. According to recent change management research highlighted in the Harvard Business Review, this rational approach may, in fact, be counterproductive:

Change leadership that emphasizes what is good about the envisioned change and bad about the current state of affairs typically fuels fears because it signals that changes will be fundamental and far-reaching. Counterintuitively, then, effective change leadership has to emphasize continuity—how what is central to ‘who we are’ as an organization will be preserved, despite the uncertainty and changes on the horizon.⁹

In other words, our manner of operation and our strategy may evolve, but our identity as a team will remain the same. All leaders who work in the corporate world have gone through changes and will go through more in the future. The only constant in business is that it changes. The most effective leaders are prepared for it, expect it, and understand how to communicate the mission to their team while it’s happening. To overcome your team’s resistance, intentionally couple your messages about the coming change with reassuring reinforcements of continuity.

One of the pioneers in leading change is bestselling author and Harvard professor John Kotter. In his book, Leading Change, he lays out an eight-stage process for guiding an organization through change. His process is one that I’ve referenced and used repeatedly over the course of my time leading teams:

1.   Establish a sense of urgency.

2.   Create the guiding coalition.

3.   Develop a vision and a strategy.

4.   Communicate the change vision.

5.   Empower employees for broad-based action.

6.   Generate short-term wins.

7.   Consolidate gains and produce more change.

8.   Anchor new approaches in the culture.

Here is an example of what that process looks and sounds like:

“This is happening within the next 60 days. Let’s get in front of it and be early adopters and LEAD the way for the rest of our organization.” At a high level, as leaders, it’s imperative that we share the specifics about the timetable necessary to implement and make changes, thereby creating a sense of urgency. Next, we need to find the leaders within our team to be part of the guiding coalition. These people are the ones who understand that change is constant and see it as an opportunity to distinguish themselves among their peers. While others are worried about the unknown and uncertainty, these team leaders will choose to lead the way. They are the core of your guiding coalition.

Next, we must ensure our ability to communicate the story and the vision is clear, concise, memorable, and useful. It must be developed and shared effectively in order to impact the team in a positive way. Then give credit and empower your team. Grant them freedom. Trust them to make choices and decisions. This is not the time to micromanage and stand over their shoulder. When it’s their decision, they will be more invested in achieving a positive result. Highlight and shine a bright light on the people who are embracing this. Create ways to celebrate and share the news of even small wins. Communicate the value of these wins to your team, especially to those who are still unsure. Finally, anchor these as part of the new behavioral norms and expectations.

Gene Kranz, NASA’s flight director for the Apollo 11 and 13 missions, said, “Expecting high performance is a prerequisite to its achievement among those who work with you. Your high standards and optimistic anticipations will not guarantee a favorable outcome, but their absence will assuredly create the opposite.”¹⁰ The same is true for the expectations you have and communications about adopting change. This “new” way simply becomes “the” way. Document it. Share it. Say it. Do it.

Coaching

If leading is about strategic vision, and managing is about administrative stewardship, then coaching is about developmental teaching. To be a coach is to give instruction delivered not to educate or inform, but to improve. For the manager of a team, coaching in this manner falls into two types: coaching for professional development (performance) and coaching for personal development (growth).

Coaching for Performance

The best coaching for performance happens in the moments closest to when the performance happens. These regular, immediate bursts of micro-coaching should happen daily. Helping your team make the minor tweaks that improve their skill level doesn’t require huge chunks of time devoted to training efforts. Rather, it is in the moments and minutes—both planned and unplanned—that may seem to those above you as inconsequential. Coaching that works in developing people’s professional skills only comes from those who are competent at the craft. So, as the head coach of your team, you’d better know your stuff.

When I switched from leading a team that sold to lawyers to leading a team that sold to clinicians, the dramatic differences between the products and industries made for a humbling experience. I had to spend a lot of time learning the new industry, the verbiage of what was a veritable foreign language to me. But just because it was going to take time for me to learn the lay of the land in my new professional world, that didn’t mean I could avoid engaging as my team’s coach until that happened. While being mindful of what I didn’t know and working diligently to close the gap, I was able to still offer micro-coaching moments that were industry agnostic, such as the fundamentals of communication skills in the context of business-to-business sales (how to open a meeting, follow-up questions that could have been asked, how to structure a proposal email, ways to secure the next appointment). These skills are as much a part of coaching moments for performance as is subject matter expertise.

Coaching for Development

Coaching for the personal development of your employees involves more long-term thinking. In this mode of teaching, your goal is to help them grow as a person in ways beyond their job performance. This requires having conversations about their career ambitions in a focused, one-on-one setting. Or sharing with them books, podcasts, or other tools for self-improvement aimed at their individual needs and strengths. These development conversations are a critical tool for creating the type of culture where people want to do their best work. When people know their boss has their long-term interests at heart, while also working on short-term ways to help them improve their work, the quality of their performance improves dramatically. In fact, if you embrace the concept of a leader doing both types of coaching, you’ll be surprised at the new levels to which your people’s “best” rises.

This requires a willingness to do the necessary hard tasks and then go beyond what most will do. That means making the effort to learn about each one of your direct reports in meaningful ways. What are they like as people? What are their interests outside of work? What is their individual motivation? Why do they work? What are their spouse’s and kids’ names? What could you do to assist them long term? How could you help them develop their career and prepare them for their next phase? How can you help them get promoted? How can you help them improve with a current project they are working on? What specific tweaks can you offer to help them improve as a performer? Answering these questions is critical to coaching your team well. And you can’t answer these questions without getting to know your people and their work really well.

Believe it or not, there may be people in your organization who do not support you leading your team in this way. You may even have one of those people as your boss. I did, once. He disliked that I devoted so much time to the development portion of my coaching. He cared about short-term results and felt that my caring about the long-term excellence of the people on my team diverted time and energy away from generating those results. If you firmly believe as I do that it is our job as leaders to help our team members be successful long term, that “my success can only follow the success of my team,” then you will have to create a plan for how to manage the resistance you may encounter from others. This is especially the case if the people you are helping to improve end up getting promoted to new jobs and leave your team, taking their production with them. Yes, that may cause you to have to answer to your boss, who just wants your team to keep hitting its number. But to that headache, I ask: Don’t you want to be the leader who helps other people progress and grow? Being known as the manager who does that is something to be proud of and will ultimately help you in the long term more than any short-term result you can achieve.

Ask, Why Did You Win?

It’s common for leadership teams to do a “root cause analysis” when something goes wrong. Something didn’t work the way we wanted it to, so we need to learn why. Multiday summits are held in which the group comes together to deconstruct the failure and to analyze why something went wrong. And that’s fine. But too often, managers in their coaching capacity operate the same way. In doing so, managers skip right over one of the first questions I always ask someone after they’ve achieved some levels of success: why did you succeed?

Failure analysis is valuable and should be done. However, the problem I’ve seen too often is not utilizing a form of after-action review following a successful outcome. It’s understandable why: who wants to take the time away from celebrating a win and getting ready for the next challenge to dig into the analysis of the work we just did when it was successful? When you exceed your goals, metrics, or objectives, that is precisely the best time to take a moment to pause, reflect, and understand why it went well. Maybe you just got lucky? Then again, maybe not. As the leader, it is critical to know which one is right, and understand why something worked. You want to duplicate it, and you can’t duplicate what you don’t really understand. When I spoke with Michael Lombardi (former NFL general manager and winner of three Super Bowl rings), he shared a story about his time working with Bill Belichick, head coach of the New England Patriots. Most would argue that he’s the greatest coach in professional football history. He’s won six Super Bowls (and counting). Lombardi said, “Coach Belichick always wanted to know why. After a big win, we did more analysis than anything I’ve ever seen. We learned the intimate details of every single play to better understand why we won and how we could get even better. That’s why he’s won so much.”

Here are some practical tips to help you do this.

Keep a Daily Diary

Knowing how you were feeling, why you made the decisions you made, in specific moments throughout the course of the year is critical in gaining an understanding of why something worked. Derek Sivers, entrepreneur (founder of CD Baby) and writer, shared why he believes it is important for us to utilize a daily diary:

We so often make big decisions in life based on predictions of how we think we’ll feel in the future, or what we’ll want. Your past self is your best indicator of how you actually felt in similar situations. So it helps to have an accurate picture of your past. You can’t trust distant memories, but you can trust your daily diary. It’s the best indicator to your future self . . . of what was really going on in your life at this time. If you’re feeling you don’t have the time or it’s not interesting enough; remember: You’re doing this for your future self.¹¹

Over the course of your career, you will thank yourself for keeping track of what was happening in the moments that preceded success. What were you thinking? What did you learn from your team? What did your boss say or do that had a positive or negative impact on you? By writing these down, you are connecting the dots that, in the future, you will be able to look back and connect into a picture of how your success was built.

Keeping a journal is also a fantastic tool for preserving the wisdom of perspective. Will Guidara, owner of New York’s award-winning Eleven Madison Park restaurant, shared the fantastic advice his dad gave to him when he was young. “When you’re a busboy, you have the perspective of a busboy. As soon as you become a waiter, you forever lose the perspective of a busboy. As soon as you become a manager, you forever lose the perspective of a waiter. My dad always made me journal, so that I could be the most empathetic leader that I could be one day because I would be able to actually go back and read my notes and have a greater capacity to connect with where the people I was leading were at in that moment.”¹²

Interview Your Team

Don’t wait for something to go wrong to have the deep conversations with members of your team. Analyze why they had a great year. Gather the commonalities among the top producers and performers on your team. What do they actually do all day? Approach each team member with a curious mind and a desire to learn about the business that each of them is running.

When I was managing my inside sales team, I would invite senior leaders of the business to sit with sales professionals on my team to watch and listen to how they operated. One particular sales professional on my team was the top producer in the entire division of the business. One of our C-suite leaders sat with him for an hour. Afterward, I said, “So, what did you learn?” He replied, “I was blown away by the mastery of this young professional and the speed at which he operated. He’s created a system for himself to quickly do all of the administrative tasks of the job (emails, proposals, list creation to call, etc.). This allows him to speak to more prospective customers than the average person. He also has a great follow-up system in place so that nothing ever falls through the cracks, and he’s on top of his entire deal flow.”

The high-level leader then took what he learned from the sales rep on my team and shared it with others throughout the organization. This practice of studying and interviewing the top performing people can have lasting impact on both the employee and others. One, it helped other people at the company. Two, it shined a bright light on one of our best performers, thus branding him as not only a top performer but as someone whose methods could help others. That employee felt immense pride that his production and the way he achieved it could lead to the success of others. This multiplying effect had lasting positive impact on his career moving forward.

Interview Your Heroes

There is so much wisdom out there to be shared if you’re willing to ask. In addition to regularly recording interviews for my podcast, The Learning Leader Show, with leaders from all walks of life (CEOs of large companies, entrepreneurs, Navy SEALs, professional athletes, coaches, bestselling authors), I have a regular practice of interviewing other people I look up to by email. I find the practice of asking someone—your favorite boss, a parent, or a leader in your community that has positively impacted people—to sit down and write their answers results in thoughtful and useful responses. Often, the person I’m “interviewing” in this way will thank me for “forcing” themselves to do that deep, introspective work. Some of my greatest learnings have come from doing this exercise on a regular basis.

Because of my positive experience with it, I’ve made this an assignment for the people I lead in my Learning Leader Circles and in my online course, The Learning Leader Academy. The feedback I receive from those I push to do this is often proof positive that my experience wasn’t the rare exception. Here’s what one participant shared with me: “Just received the answers back from my all-time favorite boss. The answers were incredible! It prompted a phone call, which then led to a meeting. I had not seen her in 10 years and now we’ve reconnected because of this exercise. Thank you!” So much good can happen from putting yourself out there and asking someone else what they think. It can reconnect you with past friends, colleagues, and mentors while putting you in the driver’s seat of your learning. Make this part of your operating framework moving forward, and I promise you will not regret it. In fact, I would love to hear how this goes once you start doing this. Email me ([email protected]) after you’ve tried it, and let me know how it impacts you.

Training

Sales trainer and keynote speaker Phil Jones recently asked me: “Would you choose to be good, better, or at your best?” Without thinking, I instantly responded, “My best!”¹³ That’s the mistake nearly everybody in the world makes, Jones says. You have already outperformed what previously you would have called your best. We tell these lies to ourselves and say things like, “I tried my best.” But if we honestly looked inside ourselves, we would realize we could have done better. We should all focus on continually getting better, not getting to the best. We will be in the chase of our best forever, knowing we’ll never reach it. Practice and training are the exercises of that chase.

I learned through the grueling practices of Coach Ron Ullery the benefit of making practice harder than the games. We endured what felt like an endless degree of repetition to focus on perfecting the tiny details and most basic fundamentals. On top of being both physically and mentally better conditioned than every opponent we faced, we had also built up an amazing amount of muscle memory so that, by the time of the game, our bodies’ execution had become nearly automatic. Legendary NFL coach Bill Walsh believed that mastering the basics was the best strategy for succeeding in pressure-packed situations: “I might do even less strategizing for a Super Bowl game, because in the midst of the extreme pressure I placed a premium on fundamentals.”¹⁴

As a manager, I wanted our training sessions to make for a more challenging experience for my sales professionals than their actual sales calls. Training should be part of your weekly schedule. Some should be led by you (the manager), while others should be led by team members. Design an environment that is challenging while practicing, so that it creates a more “automatic” response and comes more easily when it’s for real. As part of the training and practice regimen adopted by New Zealand’s All Blacks rugby club, they focused on the Greek word automatus, which means “self-thinking.”¹⁵ Prepare so that your team creates performance instincts and does not have to “think” when they’re on the field. Professional downhill skiers do this daily by “setting their edges” before racing down the mountain—a small but important maneuver to remind themselves of the tiny details they worked on in training.

As the manager of your team, it is up to you to cultivate an environment in which training (or practicing) becomes ingrained in the culture. During the interview with my dad for my 300th podcast episode, he said something that really captured the point about this:

You can be at the top of your profession and still work on the tiny details of your craft every day. It’s amazingly important. And if you can’t take inspiration from that, then you just don’t get it. I went to Japan one time on a trip and I got to visit a sales office, and I saw all over the office all these Japanese citizens who were salespeople there practicing the appointment they were about to go on over and over and over. How they’re saying the words, how they’re responding to objections, and I thought, This is the way it’s supposed to work.

Sometimes, ensuring your team is properly trained means bringing in someone else to teach them. When a subject matter expert is required to help your team get better, it’s your responsibility to find who could best fill that need and invite that person to speak to your team. If there is a new product rollout that would benefit your team to know more about, invite one of the key designers of that product to give a presentation and then listen to your team share what they’ve learned afterward. Develop a process in which they take what they learn, distill it to its essence, and explain it clearly and concisely. Create a consistent learning environment in which training and learning is just a part of the fabric of your team.

Jerzy Gregorek, world class weightlifter and creator of The Happy Body program, likes to say, “Hard choices, easy life. Easy choices, hard life.”¹⁶ It’s much harder as the leader to create and deliver regular training. You will most likely receive pushback from members of the team. That’s OK. Doing the hard stuff now creates an easier life later. It’s akin to the quote from legendary Navy SEAL Richard Marcinko, “The more you sweat in training, the less you bleed in combat.”¹⁷ It is much easier (and much more shortsighted) to say, “We don’t have time for that. We have work to do.” That’s what most people do, and they miss opportunities to get better. To best set your team up for success, play the long game: train, train, train, and then practice, practice, practice.

THE FREEDOM OF HUMILITY

Joshua Becker, bestselling author of The More of Less, writes:

[Humility] grants enormous power to its owner. Humility offers its owner complete freedom from the desire to impress, be right, or get ahead. Frustrations and losses have less impact on a humble ego and a humble person confidently receives opportunity to grow, improve, and reject society’s labels. A humble life results in contentment, patience, forgiveness, and compassion.¹⁸

I have chosen to close this chapter on getting results by focusing on what usually gets tossed overboard when positive results start rolling in: humility. It is often said that “Humility is not thinking less of yourself, but thinking of yourself less.” In doing so, you free yourself to perform and help others do likewise without worrying about you. There is great power in leading with a service mindset that says it’s your job to help other people be successful. Knowing this from the beginning is a good way to start. “The battle,” Brian Koppelman told me, “is to accept who you are while not giving up on improving yourself. To continue to try to become the perfected version of you which you can never be. And to accept your own frailties and faults.”¹⁹

For me to learn this, it took time, some maturity, and help from others. As a new, hard-charging, cold-calling new business sales professional, I looked out first for myself in my quest to get to and stay at the number one spot on the weekly stack rankings. As someone who got used to being at the top of those rankings, it was humbling (and at times, humiliating) to take over the team that was dead last in the rankings. All of a sudden, my name was attached to a team that was performing at 77 percent of plan. Nobody wanted to hear my excuses: “Well, I’m new and these aren’t the people I hired,” or, “I need some time to get us back on track.” While those may have been true, I immediately became responsible for the results of my team the instant I become the manager.

Regardless of the new challenge ahead of you, the last course of action you should take is to separate yourself from the group because you are unhappy with the current results. Trust me when I say this: the best way to avoid doing that is to make humility a central piece of your mental leadership software. When you take the posture that it isn’t about you, then you can avoid doing things to save face and get down to doing the messy work of helping your team excel. I urge you not to make the same mistakes that I have made and to learn this earlier in your career. It will serve you (and the people you lead) much better. As investment CEO Brent Beshore told me, thinking of life in a serving versus served mentality, “The more I give with no expectation of reciprocity, the better life goes. For others and for me. [It’s] counterintuitive and countercultural.”²⁰

I asked one of my favorite (and most effective) bosses, Dustyn Kim, about her ability and willingness to say the words “I don’t know” and to regularly share her fears and vulnerabilities with her team (I was a director at the time, and every member of our team was that level or higher). This is what Dustyn told me in response:

This approach is definitely a natural instinct for me. Having said that, I had moments when I transitioned to a larger general manager role where I questioned that instinct. I wondered if I would be respected by the team if I didn’t always have a clear path and most, if not all, of the answers. As I grappled with that, I realized it wasn’t going to work for me for the following reasons:

1.   I’m not that good of an actor/wasn’t sure I could pretend to have all the answers;

2.   It would lead to me putting a lot of pressure on myself, and given my high personal standards, would likely lead to me feeling like I was constantly failing; and

3.   Most importantly, I realized that some of the best answers to our challenges were likely to come from the team (both my direct reports and the broader team that was in front of the prospects and customers all day every day).

Plus, I knew that if you all felt involved in crafting our path forward you would be more likely to support it and engage in a more meaningful way. It was really scary at first to be that exposed on such a grand scale (e.g., being mic’d up with lights shining on you as you look out at a huge audience of people that you need to lead and inspire), but once I tried it, the positive feedback loop that resulted told me I was on the right path.

Dustyn never once used the word humility. Fitting, because that’s exactly what leading with humility looks like.

MANAGING UP

What do you do, though, when the people you are responsible for delivering results to aren’t examples of humble leadership like Dustyn? One of the most common emails I receive from listeners of The Learning Leader Show goes something like this: “Ryan, I am all about personal and professional development. I read books, watch TED talks, listen to your podcast. I’m always trying to learn more and improve. However, I work for a boss (or bosses) who don’t show any of the same curiosity that I do. They have the mentality that they’ve got it all figured out. And I’ve found that while they are decent people, they definitely don’t have it all figured out. . . . What should I do?”

Managing your boss (and your boss’s boss, etc.) is a challenge, and yet it’s a skill that can be developed. If you choose to work in an organization where you have a boss, remember that part of your role is to make their life easier. Regardless of their mindset toward growth and any other disagreement you may have, if you want to remain working for your current company (and that boss), then you should be focused on two things: (1) serving the people you lead, and (2) helping your boss be successful.

Often, it is easy to judge the boss or CEO as being a bad leader. We’ve all done it. From our point of view, there are obviously things that we would be doing if we had that job. But therein lies the issue. We are looking at it from our point of view, not theirs. Be careful to judge someone too quickly when you don’t have the full picture. We are all imperfect—just in different ways.

The most important aspect for us to learn and decode regarding leaders whom we find lacking is their intentions. Do they have positive intentions, wanting to do the right thing? If yes, then chances are their ability to effectively lead is being hamstrung by a lack of knowledge, skill, and/or experience. If that’s the case, we can work with that. We can offer ideas. We can, carefully, pick our spots to “coach upward.” We can share with them how we feel when they act in a certain way that causes problems for us and others (because odds are you’re not the only one feeling the negative effects of ineffectual leadership). In short, we can find ways to work with good people who do bad things because, as good people, they are likely able and open to taking constructive feedback that is given in a positive fashion. As Hall of Fame coach John Calipari told me onstage at an event at the 2019 NCAA Final Four, “You can have a bad deal with good people. Stuff happens. But you can never have a good deal with bad people.”

If, on the other hand, you determine that this leader is acting in a willfully negative fashion, not caring how their behavior impacts you and your team, then you have some hard decisions to make. In that situation, it may be time to take the long-term view and start looking outside of your current organization for opportunities to grow your career. Take great care in studying the situation and the leader you have concerns about. You must ultimately decide what is the truth about the person and choose your response accordingly: (a) stay and coach, give feedback, and speak honestly, or (b) get your résumé together and begin your search for an organization that is a better fit for you. This is not a choice to make lightly because it is not a decision you want to get wrong.

One key point to remember: it is important that you don’t show your frustrations with your boss to the team that you are leading. As leaders, we have a responsibility to bring optimism and enthusiasm to our team. We cannot allow ourselves to take the easy path of dumping on the boss in front of them as this will not help them to be their best. Doing so will only drag them down into a valley of frustration as well.

One of the best ways you can coach or manage up is to build the culture and habits you want to see on your own team, generate winning results from it, and watch it spread. Let your results preach the gospel of leadership that is humble, management that is creative, and coaching that trains hard. Build it from within and watch it spread. This is a long-game play. It takes time and requires high performance on your team. Soon enough, other groups in the organization will be asking you how you did it, what you did, why you did it, and how they can do it, too—developments that can convert even the most skeptical of bosses to your cause.