Every day, Chris Holmberg tries to put himself out of business. As an executive coach for nearly two decades, he’s worked with leaders of tiny startups and multinational corporations alike. But the core of his practice remains pretty counterintuitive: There’s no solution. No secret sauce. He doesn’t claim to have magic formulas for building teams or running meetings or tripling ROI. Instead, he’s in the business of building mindsets that can handle anything.
Holmberg works with his clients to uncover dangerous and unproductive patterns in their work, thoughts and behavior — the traps that hold them back from their potential. His secret, which he willingly and eagerly shares, is training people to uncover their own self-limiting mental habits and destructive verbal patterns. Only then is transformation possible.
In this exclusive interview, Holmberg shares what he’s learned on the job, observing leaders of every ilk — the young and old, the new and seasoned. In particular, he hones in on the mistakes that ensnare some of the most promising people he’s met. Most importantly, he offers a simple daily exercise that can free people to see their growth and failure in a whole new light.
Holmberg can’t emphasize the power of consistent practice enough. He has a very calming, even soothing presence — you can see why he’s great at working with anxious founders — but this is one area where he holds a hard line. In this context, the word ‘practice’ means committing to continuous, daily mental rehearsals, to regularly reviewing your behavior and interactions and identifying how and when you’re standing in your own way.
“Outside the business world, many people get how important practice is. Athletes, for example, do it all the time as a matter of course,” says Holmberg. “People who perform, or play sports, or music, they all see the value of practice.” But in business, almost everyone wants to be good right away. They don’t want to spend time going over what already happened.
Mental rehearsal can seem pretty cerebral, but Holmberg’s method is actually quite concrete. And his prescription is shockingly low-lift: Spend 15 minutes a day in reflection — true reflection, in a quiet space, with your inbox closed.
Take this time to review the events of the previous day and make plans for the one coming up. You can write these observations down if you want. You can reference your calendar to reflect on the day’s interactions and prepare for tomorrow’s. Whatever will ground you in the ritual.
At the end of every week, Holmberg asks his clients to run the same exercise for an hour, only this time reflecting on the past week as a whole and considering the the challenges and opportunities of the week ahead.
To a busy founder, taking a whole hour might seem like a waste. But that’s exactly the type of leader who can’t afford to not take the time, he says.
Startup leaders can’t afford to have low learning efficiency. They must milk each experience for maximum learning. Reflection is the key for accelerating your learning curve.
Even if you’re ready and willing to spend the time, very few people know where to begin. To give them a starting point, Holmberg has developed a checklist to make the time count.
“It’s a simple construct taken from something called ‘integral theory’ that encourages you to look at the world through the lenses of the ‘It’ the ‘We’ and the ‘I,’” he says. “The It refers to your tasks, the external stuff of your role at work: Your goals, achievements against those goals, the stuff you’re getting done. The We is about your relationships, the quality of your interactions — which too few people think about. And the I is about the attitudes and energy you personally bring to the table every day.”
When he works with his professional clients, he wants them to think about their experiences through each of these lenses and ask themselves, “Were they thinking like an executive? Like they would want to be thinking as a leader?”
“A lot of startup leaders were just engineers or product people yesterday,” he says. “Under pressure, we all revert to the things we know and feel comfortable with. These moments of reflection are your chance to review and gradually shift your mental models to leading, not just executing.”
These are the questions you can ask yourself to methodically revisit your day:
The It: Did you execute your work — the emails you wanted to write, the strategy document you owed your boss — the stuff you had on your list at the start of the day? Did you do the things that were important and not just urgent?
The We: Did you add value to the lives of the people you interacted with? Did they walk away with more knowledge, energy, goodwill, help, a better understanding? “It’s not asking whether you made people happy,” says Holmberg. “That’s not always the goal.” You want to make sure you communicated clearly in a way that added value for them and met goals for you.
The I: How did you manage your own energy and mood? Self-care measures like working out, eating well, and sleeping enough are just as important as anything you do in the office. Ironically, those are the things most startup leaders drop first and yet the “I” is the foundation of leadership. You can’t help others if you deplete yourself.
Startup execs commonly become overly focused on the ‘It’ and moving forward at the expense of the ‘We’ and the ‘I.’
After you’ve reflected on the day gone by (it’s good to run this practice in the evening shortly before bed), you can use the same three lenses to set your intentions for tomorrow. Here’s a template:
The It: Establish the tasks you intend to accomplish during the day and realistically acknowledge the ones that you won’t be able to finish. Do you have meetings during the day? If so, do you know what they’re each for? Do you know what you’re trying to accomplish during them? Do you have your agenda for reaching those goals?
The We: Do you anticipate having challenging interactions? For example, do you have any meetings with a colleague who you know is frustrated with you or the company? Think about how you want to show up to that conversation. Consider what he or she might say that will trigger you to react badly. Mentally rehearse how you’d like to respond instead. Write it down, internalize it. Make that your intention.
The I: What biases do you bring with you? How can you see through them? How can you set yourself up to make good choices throughout the day (i.e. keeping energy high, your body fueled, etc.)? What might cause you to step off track? What is the right course of action? Identify it ahead of time.
“I was talking to a startup CEO recently, and he was telling me about an executive who wasn’t working out. He had decided to talk to her about parting ways, and was going to see her at a public event. He knew it would be a terrible choice to talk to her about it at the event, but he told me, ‘I know I’m going to do it. I’m going to be impulsive and pull the trigger,’” Holmberg says. “So I said to him, ‘No, you’re going to remember the conversation we’re having now, and use it to make the right choice.’ Coaching, in a lot of ways, is about reminding people that they can make a different choice, and inviting them to hold themselves accountable for their choice.”
Your daily and weekly reflections are all about creating accountability. Practice, in this context, isn’t about skills training. The CEO in the story above, for example, is highly adept at what he does. It’s about the practice of making good choices. “Set your intentions, and you raise the probability that, in the moment, you’ll make the choice that you know is the right one, or at least representative of how you want to think and behave,” Holmberg says.
Don’t just focus on what you want to do, either. Take the time to go over what you absolutely don’t want to do too. “Ask yourself what’s important to you. What are things you have the unique ability to do? If you get asked to attend a certain meeting, what is one knee-jerk reaction you want to avoid? What’s one unique contribution you can bring?”
Most people’s impulse is to acquiesce to demands made on their time and energy. They don’t want to let others down. Countering this pattern requires forethought and the deliberate decision to spend your time on activities where you uniquely add value, not just reacting to your or others’ desires. The only way you’ll know how to allocate your time ideally is if you take a moment to truly think about it.
“A person generally gets 5% learning efficiency out of an experience — i.e. they retain about 5% of whatever they were exposed to,” says Holmberg. “You can drastically increase that percentage by reflecting on things after the fact, and being intentional about things in the future. What’s the goal of the 15-minute practice? Consciously reflecting on the events of your day. Use those observations to construct learnings. Apply those learnings to the next iteration tomorrow.”
Each of these traps, Holmberg notes, is rooted in binary thinking — that is, rigid adherence to one of two opposing ideas. So it follows that the way out of each trap lies in taking the middle path (in fact Holmberg’s business is called Middle Path Consulting). Seems intuitive, but very few people even see the middle option, much less choose it.
The Knower Trap: Either my worldview is right or I have to blindly accept yours
This pitfall boils down to the need for certainty, which manifests as either arrogance or deference. “If a leader has to be the smartest person in the room, they’ll probably hire experienced executives but never listen to a thing they say. It’s more important to them to prove they’re smarter,” says Holmberg. “On the other side, a deferential person would hire someone they can follow without questioning most of what they say.”
Whichever way you go, you’ve forgone thought and deliberation in favor of certainty. This is no good for startups. Startups thrive on collaboration, particularly leaders who can readily admit that they don’t have all the answers but they still have an opinion.
Acknowledging uncertainty is one of the smartest decisions you can ever make.
Watch out for these polar positions: arrogance and deference — in your relationships with customers too. “Often you’ll see startups flame out because they couldn’t adapt,” says Holmberg. “They were so sure they had the right app, the right idea, but they could never take and integrate customer feedback telling them otherwise. On the other hand, you see companies that completely change their product again and again whenever a customer says something different.”
How to get out of it:
Replace arrogance with confidence. And swap deference for humility. These might sound like very fine distinctions, but in making them, you’re retaining your power while combatting ignorance. Once you trust yourself to think critically about others’ opinions and humbly adjust your own when necessary, you’ve found a healthy middle path: openness.
That’s not to say you need to leave all options on the table indefinitely. There are many times when it’s perfectly appropriate for a leader to make a choice and move on immediately. Confident leaders listen carefully to other points of view and then act decisively. If you repeat this over and over, it will encourage your whole team to keep sharing their best ideas.
The Victim Trap: It’s not my fault or it’s all my fault
Our customers are idiots. I had the right idea but my team failed to execute. My board doesn’t give me the support I need. The market sucks right now.
Excuses that are far too common. Leaders who fall into the Victim Trap have arrived at a chasm between where they are now and where they want to be — and they’ve decided to look to external factors to explain it away. If the fault can be traced to something outside their control, they can’t be held accountable. Obviously, this approach has its downsides.
There are also leaders who only blame themselves: I’m just impatient. I wasn’t born a ‘people person.’ I can’t control my temper.
This is another take on victimhood and powerlessness. “People become even more helpless when they blame themselves. In a way they’re saying they’re out of control because they were born that way. They convince themselves they just can’t change,” says Holmberg.
How to get out of it:
Turn your focus from blame to accountability and invest your energy only in the things you can control. Here’s a quick trick for shifting gears when you find yourself playing the victim: Ask yourself, “What’s my next move?” With those few words, you bring your focus back to the next step, the next action you can actually take. Plus it breaks the situation down to a manageable size.
“If I’m telling a victim story, the probability that I can change things is zero,” says Holmberg. “If I’m telling an accountability story — if I’m dealing in decisions and actions that I can control — the probability of change is greater than zero.”
At a startup, the difference between zero probability of change and any value greater than zero will make or break your success.
The Sucker’s Choice: I have to give up on either who I aspire to be or what I want to achieve
Like the other traps, the Sucker’s Choice is a product of binary thinking — in this case, the belief that you can either win or play the game honorably, but not both. Think Lance Armstrong, or Enron. Ultimately, you can’t control whether you win the game, but you can control how you play. And at the end of your career which will matter more?
Too many entrepreneurs Holmberg has encountered believe that achieving their goal will come at the expense of their personal values. This happens more often through small hypocrisies than large ones, like not being completely honest with a potential investor because you want to close a round of funding, or over-promising to a customer while hoping engineering can pull off a miracle, or committing to show up for a one-on-one and blowing it off because you got distracted.
Consider the most common manifestation of the Sucker’s Choice in the startup world: “I have to run my people into the ground or we won’t be successful.” Of course it’s possible to build a great company and treat people the right way — studies have proven it again and again.
“In the long run, success and employee happiness are tightly correlated,” Holmberg says. “When you’re in this trap though, you believe that key values are mutually exclusive. You’re a sucker if you accept this. You’re Luke Skywalker joining the Dark Side to rule the universe. In every hero story, there’s a temptation — but it’s a false temptation.”
How to get out of it:
Once again, the first and best way around this trap is self-awareness. Train yourself to notice when you’re up against this type of false choice. Situations like this are marked by anxiety that you’re sacrificing something you don’t want to. Let this be your trigger to pause and reflect on whether you really have to give something up.
“I’ve worked with leaders around the world, and when we do exercises to reveal their aspirational values, the results are always the same from Beijing to Chicago,” says Holmberg. “The list of values that emerge include things like perseverance, integrity, honesty, treating people with respect, having passion for what they’re doing. When people are self-aware, and not tired or stressed, they’ll usually choose these type of aspirational values. If their defenses are down, though, they’ll choose safety and immediate gratification — cake over the gym.”
This is when setting your daily intentions — and rehearsing preferred responses — really pays off. For each challenge you anticipate facing, get clear on two things: 1) what is the result I want? (define winning). This will help you choose your strategy. 2) How do I want to show up? (define personal success). This will help you keep the discipline of operating within your values.
Not sure if you’ve fallen into any of these traps? Listen to the words coming out of your mouth (or simply running through your head). Language is the fastest way to examine your mental models. Surprisingly, changing the way you speak can dramatically transform many other things in your life that don’t even seem related.
Own your opinions as opinions.
Take this simple example: When you say, “It’s cold out,” you may think you’re stating a fact. Really, though, you’re imposing your experience as the truth. Similarly, if you hear yourself say, “This is the wrong direction,” or “This is right,” you’re getting caught in the Knower Trap. You’re stating opinions as fact, leaving no room for anyone else’s opinions. Your words are constructing a single, unassailable world view. And once you hold tight to that perspective, there’s no room for fresh data or critical thinking. In many cases, you have shut down conversation.
A good leader aims to get the best ideas out of their team. To do that, use open-ended language that sparks discussion. Swap “you’re wrong” for “I see things differently.” When you do, you open the floor for other people’s thoughts. Why do you see things differently? What’s everyone else’s take? If you’re concerned that a strategy will fail, you should absolutely voice that, but try, “I have concerns” instead of “That won’t work.” Remember that being open does not mean being indecisive. You can make a decision without having to convince everyone else that you are right and they are wrong.
Own your actions.
Language can tell you when you’re teetering on the edge of the Victim Trap too. Imagine that someone walks in late to a meeting you’re running. You might say, “We had to wait 10 minutes for you! Now we’re starting late!” Seems accurate, right? “You have to ask yourself, though, ‘Am I holding that person accountable or am I blaming them?’” says Holmberg.
When you imply that someone else has controlled your behavior, you’re blaming them — it’s the other person’s fault and you’re innocent.
This scene could easily play out another way. You start the meeting on time without them. When your colleague walks in, you could say, “Hey, we agreed to start at X time. What happened?” Given the chance to respond, they might have a solid explanation. “In this scenario, you swap blame for accountability. You hold yourself accountable for the start time of the meeting, but you’ve also held your colleague accountable for their decision to not be there on time,” he says. “From there, you can set up the best possible choice for next time. Maybe they shouldn’t let client calls delay them from being on time in the future. Maybe they should always text you if they know they’re going to be late.”
The goal here is to recast your statements so that you don’t feel powerless. Your words should make it clear that you’re not only in control, but you can also take a positive next step.
Own your decisions.
Be sensitive to language that allows you to pass the buck. It’s often subtly coded, so an untrained ear may not notice it. Take this common business-speak: “Your promotion isn’t going to happen.”
“Look at how subtle that is,” says Holmberg. “As a leader, I can absolutely disown responsibility for that decision and imply that it’s the result of any number of unnamed external factors.”
Now consider the alternative: “I have decided not to promote you this cycle for these reasons.”
“Which leader would you rather work with?” he asks. “The latter, of course. Both parties know who made the decision, and by being honest about that, there’s now real opportunity for open dialogue — and a real opportunity for the employee to make the changes they need to get ahead.”
Deflection of responsibility is particularly pervasive at startups, where leaders are often at the helm of a team for the first time. A corporate manager may have had 15 years to climb the ladder — but if you went from individual contributor to CEO last week, you’ll have to find a way to learn the same lessons quickly. Consciously reflecting on your actions, right down to the words you choose to express yourself, is one of the most powerful ways a new leader can grow.
Failure is an extremely important tool for successful leaders. Research has shown again and again that all great leaders share a common trait: Empathy. And that’s telling.
The only people who have great empathy are those that have suffered. The least tolerant people in the world are the ones who have never failed at anything.
“Leaders who have never failed are fragile,” says Holmberg. “They see the world divided between winners and losers, and they desperately want to avoid falling into that latter category, so they never try new things. If they tried something new, they might fail, and that would ruin their streak. When this type of person manages a team, then no one can fail, and that sets up a really terrible environment.”
When a manager empathizes with failure, they don’t point fingers or chastise anyone. Instead they say, “I get it. Let’s talk about why this happened.” That doesn’t mean they’re accepting a poor outcome, or giving their reports a pass. In fact, they might be even tougher, because they’ll demand that people learn from mistakes. “The ROI on failure is learning,” says Holmberg. “But only someone who has failed can see the extent of this truth and its worth.”
Even more advantageous, a leader who has made peace with failure can separate their own self-worth from company performance. “If the source of my identity is winning the game, then my happiness is bound to be very, very inconsistent,” says Holmberg. “Ultimately, I have little control over the outcome of the game from day to day, so that’s a lot of up and down. This is something I see all the time at startups — a miserable cycle of highs and lows that ends up dragging everyone on the team down.”
When you neutralize the specter of failure, you can play to win with intensity and intelligence, knowing that sometimes you will lose without stressing about it.
“When that happens, when you’re proud of how you played the game, you can walk away with a sense of self that makes you resilient the next time you try something,” he says. “Ironically, and I’ve seen it happen before many times, you win more if you let go of winning.”
If you go into a fundraising pitch consumed by how much you need that VC in your round, odds are much higher you’re going to be nervous, ungrounded, not your best. If you go in focused on what you care about as a founder and what you genuinely want to do with the funding, your presence will be far more compelling.
Holmberg has a surprising rule for his coaching clients: “If I’m still working with you on the same stuff after a year, you shouldn’t be paying me anymore.” At that point, nothing is budging. Either the client is not making choices that will allow him or her to improve, hasn’t committed to regular daily practice, or there’s some psychological block they’re unwilling to address. Learning the tools to succeed is one thing. Actually using them is the way growth happens.
There’s a reason new business books come out all the time and still find an eager audience. Too often, people consume the information without actually internalizing it and putting it to work. “It’s like my dad used to be with exercise equipment,” says Holmberg. “He’d gain some weight, buy an exercise machine, use it a couple of times, and then put it in the garage. Of course he didn’t lose weight so he’d buy another exercise machine, repeat the process, and would keep thinking, ‘This equipment doesn’t work!’”
Leading a team better and smarter means using all the equipment you have at your disposal. But more than that — it’s about the constant daily practice you put in reviewing your past behavior and thinking about how those lessons apply to the future. Getting better is the sum total of hundreds of decisions a day: the words you use, how you book your time, whether you take a risk, and — not to be underestimated — how many hours you sleep.
With practice and the help of others (mentors, partners, coaches, etc.), you can build the habits that will dramatically boost your success and the success of your team. “These may seem like simple tools, but their simplicity means you can easily use them again and again to resolve the gaps between where you are today and where you want to be. That’s where your real opportunity lies.”