5 Ways to Assess if a Leader is Worth Following
For a higher chance of success without hating the journey to get there
Welcome to the latest entry in The Captain’s Log. You’re in good company with thousands of fellow entrepreneurs and innovators who have subscribed!
I’m your host, Bob, and my mission here is to share personal, behind-the-scenes stories of ups and downs from my career leading tech startups and corporate innovation.
I write to make you think, smile, and discover a shortcut to success or a trap to avoid.
Here we go…
Whether we are on the BigCo or Startup path, we all want our work to be a journey of growth and success. But so much of this relies on forces we cannot control. Recessions, regulations, pandemics, and many more kinds of luck are the most significant drivers. After that, I believe your company leaders are the next biggest leverage point. They create the culture, select strategic directions, ensure everyone gets paid, and much more.
We don’t have the power to change people. But we do get to choose which people we work for.
But how can we best assess a leader?
You could ask a CEO routine questions when interviewing for a job or having that first 1-on-1 with a new boss. “What’s your vision for the company?” or “Where do you see yourself in five years?” I’ve gotten those questions many times and shared the same routine answers. The thing is, they don’t really help you assess a leader. Anyone can spout some B.S.
There’s a much easier and much more effective way to do due diligence on the people you may work for: Watch what they do and listen to what they say along five fundamentals:
1. Grants Control Over Work
The cause of most depression and heartache is the feeling that we lack control over our lives. Humans want agency, and when our work is dumbed down and bereft of choice and creativity, we disengage. A leader who won’t let us call the shots makes life suck, and will never be able to scale a company to success.
Interestingly, this desire for agency is why so many leaders micro-manage. They, too, want to feel like they are impacting the business. The key, however, is realizing that supporting employees and building a strong culture are ways to touch the company, too!
Recently I heard repeat founder, Sam Parr, describe a leadership philosophy that helped him turn The Hustle newsletter into a big acquisition by Hubspot: Set expectations and guardrails, and let your people work however they think is best to get there. People can achieve great things when you get our of their way.
2. Speaks Least
A few months ago, I had lunch with a potential business partner. The person was a senior HR executive at a corporation you’d recognize, and this was our first meeting together. He spoke about himself the entire time. I’m not joking! He even failed to eat his entree because he didn’t stop to put the fork in his mouth. After an hour, I had to go, and he got his meal in a to-go box. There won’t be a second meeting.
Too many leaders are like this. They rise to a level of power and enjoy the view. They look at each meeting with a subordinate as an opportunity to feed their egos by taking up all of the air in the room. They are the first to say something and monopolize the discussion. You are their audience, not an equal.
The better leaders don’t need to feed their egos. They realize there is no value in talking about themselves. It’s much more interesting and practical to shut up and learn about other people—especially the views of employees who are much closer to where the software is written, the customer is serviced, or the sausage is made.
3. Readily Admits Mistakes
When strong leaders speak, they talk about their failures more often than their successes. They understand that mistakes are where we learn and how we improve. Their mistakes are what they want to remember—and they want those around them to be free to point out future mistakes before they are made.
As a leader, talking about your bad decisions also conveys to others that your organization is safe. When you give people control over their work, you won’t fire them the first time something bad happens.
And it makes you more human. By exposing yourself as imperfect, you build trust.
4. Sensitive to the Stage
Early in my first position leading people, a mentor taught me that “you’re always on stage.” Both consciously and unconsciously, every move you make and every step you take is noticed by the people who work for you. Your strengths and weaknesses become magnified as they modify their work styles to match yours. You’ll hear people trying to decipher the words you spoke in the all-hands—or after the third beer at the happy hour. It’s weird, but it’s people.
When my last company was still in its earn-out, our acquirer brought in a new President. He traveled to our regional office and attended a dinner with the HR team, mostly young female employees. Stories surfaced quickly from what he talked about: (1) How amazing his new car was—and how much he paid for it; and (2) The status of divorce proceedings with his second wife and his outrage that she was asking for half of his airline points. Quite a first impression! Too bad it took three years and hundreds of millions in lost market value before he was fired.
Pulling into the office parking lot in your expensive car, bragging about your ski trip to Gstaad, or wearing $600 shoes sends a signal. Of course, you can spend your money on whatever you like, but rubbing others’ noses in what you’re doing with the proceeds from the company they toil at is not smart.
A better way of living at work is to admit that everything you do and say will be noticed—and adjust your behavior to maximize the value of these impressions.
5. Smiles and Laughs a Lot
I’m fascinated by the economy of China. During my lifetime, this country of 2 billion people has gone from a backwater to the second-largest economy in the world. But it will never be the largest. There are many reasons, but I think the biggest is that its current President, Xi Jinping, has extended his leadership term, probably for life.
And Xi doesn’t smile.
The guy seems to hate his job. He’s got a permanent grimace that comes from years of unhappiness. When shaking hands with fellow world leaders, he tries to curl the corners of his mouth, but it’s like lifting cement. Forget about showing teeth.
You want to work for a leader who is happy to play the game. They break the tension, keeping people loose and unworried. They seem to, well, actually enjoy what they do and the individuals they do it with. They’re not necessarily the life of the party and certainly can have a range of moods. But they realize the value of play.
There you have it—all you need to evaluate your current or potential leader without lobbing cheesy questions or scrolling through Glassdoor. Take this list, give them a 1 (lowest) to 5 (highest) rating, and add up the scores. Here’s my take on the math from here:
21-25 - Hitch up your wagon and follow them to the end of time. If the current company doesn’t work out, they’ll nail the next one.
16-20 - Most leaders are here. The key is to look for signs of growth and improvement. Are they open to feedback and working to improve? If so, stick it out. If not, head for the hills.
11-15 - Your only chance for a win here is if the person is an Elon Musk; just realize that you’re often going to hate the journey. Meditation helps.
10 or under - G.T.F.O. A.S.A.P. This is a work life that will be nasty, brutish, and short.
This is also a handy exercise for many other business partner decisions. Startup founders should use this for due diligence on co-founders and investors. Company leaders and HR teams should use this in interviews with new executives and managers. It can be applied to evaluating various business partnerships, especially acquirers. Use it any time you're about to enter a long-term relationship with another human being—where the stakes are high, and you will have to work closely together for a long time.
And as a company leader, this is a checklist you can use in assessing yourself. As a CEO, you usually don’t do an annual review; if you do, people fear being honest in their feedback. So look at this list and think honestly about where you can improve. Then, seek help from an executive coach, close friend, or psychologist to get there.
Taking a step back, you might find that all five of these factors ladder up into one big thing:
The business is not about you and your ego; it’s about them—the people who work for you—and inspiring them each day. Think first and foremost about how you can help them succeed and have fun along the way. That’s the real key to success in work…and life.
(What am I missing? What are your favorite “tells” of good or bad leadership? Throw them in the comments so we can learn from what you’ve learned!)
How we might work together…
My team and I lead Hearty, a tech-enabled recruiting service that helps early-stage startups hire proven talent. Our senior team of repeat-exit founders sources and screens, saving you time and money. When you need help, let’s chat.
Feel free to schedule time together during my Open Hours for questions, feedback, networking, or any other topic.
Great list Bob. The only element I would consider adding is a talent/capability-building element. I have observed that the leaders who have consistently invested in building capabilities through qualitative activities (e.g., mentorship, coaching, sponsorship) and quantitative investment (e.g., formal training) are actively practicing the science of leadership. Simply: the best leaders build more leaders and have the evidence to prove it. Simple, not easy.