Without Context, You’re Killing Us
Help your team help you by sharing the Why
Welcome to the latest entry in The Workaround. You’re in good company with thousands of fellow entrepreneurs and innovators!
I’m Bob, your host. My mission here is to share personal, behind-the-scenes stories of the ups and downs of 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…
Great leaders are like artists.
They pay attention to details and aim to move people through inspiration.
While the artist must spend countless hours mastering a craft, you, dear leader, need only practice the Golden Rule.
Let’s talk about context.
I might seem to be making a big deal out of a little thing. But details are the tells of a leader’s true character. If we fail our people here, we are likely failing them—and our businesses—in much more significant ways.
Meet the New Boss
Flashback some years ago, a few days after selling my company. Suddenly, I have a boss again. His name is Tom.
Tom and I spent several hours together before the acquisition. He was a key player on the due diligence team. Our conversations were great, and I loved that he also came into the company through an acquisition. I was relieved to work with someone who had been in my shoes and would understand a fellow entrepreneur better than most corporate managers.
I’m not too concerned about reporting to someone again. I assume Tom will leave me alone if I run my business well. He’s running a separate business unit and has bigger issues to worry about than my product, which is smaller but growing faster in sales and profit.
A few days into this new relationship, I get a text from Tom:
“Could you pull the quarterly revenue numbers for your biggest ten clients from the past two years?”
“Huh,” I think to myself. I guess this is what it’s going to be like. Shit…
I have my team pull the numbers and send them over a few hours later. Tom thanks me. I file this away.
The next day, I get another text from Tom, which he sends while sitting in an Executive Team meeting:
“Hey, how many people do you have on your paid social team?”
I reply. He thanks me. I stew…
My mind races. Why is he asking these questions? Is he concerned about my business? Is his boss—the company's CEO—asking him to do layoffs? What the F is up?!
I sneak to our office’s Mother’s Room to meditate for a few minutes. I first ask myself: “Am I being an asshole here?” This is one of the constructive voices I developed soon after first managing people at work. In this case, I verify that I’m being treated in a way I learned long ago is wrong.
After a few deep breaths, with a cooler head, I remember that having a boss again will make me notice things—and cringe. Yet this lack of context is so basic that it will be impossible for me to brush off. I ain’t that Zen yet.
But I do believe in managing up and taking equal responsibility for sharing my preferences in how we work together. So after the sixth or seventh one of these mystery requests, I insist we keep our scheduled one-on-one meeting so we can talk about this.
Tom is friendly about it—even thanking me for bringing it up. He jokes that his wife has to hit him over the head on this exact point. Tom shares more of the context behind his request and promises to better loop me in. The following week or so, he’s much better.
Alas, it doesn’t last long. In the weeks and months ahead, Tom continues to ask for things without context. I get tired of writing, “Hey, I would love to know more.” Eventually, I find someone on our finance team to take on these requests. I give him the context that Tom asks for random stuff, but don’t stress about it. I’ve got him covered. It's easy for me to say (Sorry, McRyan!).
Tom’s lack of looping me in extends to much bigger things—including critical decisions about company positioning, product strategy, and team structure. Tom rolls out giant changes of direction that impact my business and in areas where I have lots of valuable experience to add. His little tells end up saying a lot.
I don’t last long, either. As soon as financial handcuffs loosen, I find my way to G.T.F.O.
I’ve sold two companies in my career. And some people who know me well might wonder which one I’m referring to here. Well, pretty much the same situation happened in both companies! “Tom” is a two-fer. Lucky me…
Why Giving Context is Critical
Giving context can save lives. Here’s an example:
Did you know that people in desperate need of a kidney often turn one down when it is offered? As described in the book Collective Illusions,
“When a donated kidney becomes available in the United States, it’s evaluated for matches and then offered on a first-come, first-served basis to the matched individuals on the wait-list. This means that, when a person at the top of the queue rejects a kidney, others in line then have to decide—on the basis of little information and with precious little time—whether to accept that same, previously rejected kidney. Like a house that’s sat on the market too long, the longer a kidney sits on the wait-list, the lower its perceived quality.”
Without context, people make deadly assumptions. The solution, which more medical systems are implementing, is to have each person who declines provide a reason that the next person in line can see, such as “I’m traveling out of state” or “It’s not a close enough match.”
In our workplaces, providing context falls under the importance of Transparency, which is one of the four key pillars of a High-Performing Organization as I describe in this series of posts.
To borrow from the analogy of a ship: When a random question is asked, or a decision is made from leadership without context, our instinct to worry kicks in. We feel less safe; there is a leak in the boat, and we’ve got to run down below and start looking for what’s wrong. Your text creates chaos in others’ lives.
In one of his lectures, investment legend Charlie Munger tells the story of how the CEO of the Braun company saw this need for context:
“If you wrote a letter or directive in the Braun Company telling somebody to do something, and you didn't tell him why, you could get fired. In fact, you would get fired if you did it twice. If you always tell people why, they'll understand it better, and they'll consider it more important, and they'll be more likely to comply.”
With simple context, we fear not. People become even more helpful.
Recently, at A2, our influencer marketing business, one of the influencers we were working with on a campaign pushed back on the 1-year content license in our contract. Our team took the time to explain that we set this term because it’s a pain for our client brands to do anything shorter, especially as launches can get delayed. Once she understood this perspective, the influencer accepted our terms.
Another recent example on the MFM podcast a story from the CEO of Applovin, a billion-dollar software company. He repeatedly asked a developer on his team to tweak a metrics dashboard. Eventually, out of frustration, the developer marched up to the CEO’s desk and said, “Let me sit with you for an hour and watch you.” This observation and discussion helped the developer understand the “why,” and he left and came back after a few days with an entirely new dashboard built specifically for what the CEO needed.
By providing your people with context, you’re enrolling them in your project and bringing more brains along to help. They may come up with better solutions than you could, and you’re building closer relationships in the process.
Back to the ship analogy: Instead of reaching for buckets in fear, they are helping you judge the wind, hoist the sail, and scan the horizon for opportunities.
Leaders Gotta Get This
In both situations, I struggled to understand how experienced leaders who had successfully built and sold businesses could miss something so basic. I also took it very personally. I wondered why they wouldn’t see value in my perspective and want to bring me into their inner circles.
Many leaders feel lonely at the top. I think that’s because they can become isolated from the employees, clients, and partners that make up their businesses. The power leaders gain can create distance. Power makes it easy to ask for and get whatever you want. And almost no one is confident enough to call leaders out on their weaknesses.
We must also remember that getting a leadership position or selling your company comes down to many factors other than empathy—including plain old luck. But luck cuts both ways, and a bad habit like this will eventually hurt one’s career.
If you are in a leadership position, build this insight into your daily interactions with your team. Realize the power of your asks, and add the context that turns fear into love. Funny, I do this so much that I even find myself writing context into the request box on ChatGPT—and I get better results!
Pay attention to specific situations where you should give more context than usual. For example, this week, I was chatting with the CEO about a new business we’re launching soon. In explaining something new to her, I started by saying:
“My normal bias is to assume you’ve got it under control and will come to me for help. But I will go into deep detail on this specific topic because it’s an area where I have a lot of experience, and you’re doing it for the first time.”
Basically, I’m waving a giant flag and saying, “Here’s why I’m saying this to you!” She might think I’m weird, but it works well. And she might as well know I’m weird, too.
At a minimum, providing context is a basic courtesy—like saying Please and Thank You. At maximum, you’ll get much more value than you asked for. Your team is here to carry the burden of leadership with you and make it a little less lonely.
If you’re on the other end of a leader who fails to share context, like I was, I believe it’s worth addressing it directly. While it didn’t work for me, it worked for the Applovin CEO above. Younger leaders, in particular, don’t have anyone teaching them this stuff, and you can sometimes manage them up into a form that makes them better for you and countless others for the rest of their careers. I’d probably be in a ditch somewhere if my team members didn’t provide timely feedback on my leadership failures.
If they don’t change, well, realize that it’s nearly impossible to change people. Then it’s up to you to decide whether or not to suck it up or abandon ship. I tend to think you deserve better. Life is far too short.
This is the Art of Leadership
Leadership is a lot simpler than we tend to think. Leaders exist to rally people to a task. So, the better we work with people, the better leaders we will become, and the more successful our tasks will be.
It doesn’t take giant salaries, team offsites, and big-screen desk monitors to motivate people. It certainly doesn’t take getting a business school certificate or implementing EOS. It’s about leaders putting themselves into the shoes of the people they lead. And these are primarily eternal lessons that have been at the core of positive human behavior for millennia, like good manners and the Golden Rule.
We’ve just got to add more humanity to business.
I had another interesting conversation this week with a prospective business partner. This is the fourth time we’ve talked, and we further peel the onion on each other each time. In this latest chat, we agreed that the business niche we’re exploring together is not our deep passion—it’s far from curing cancer. Instead, we are passionate about working with people we trust and enjoy. This makes whatever we do more successful and special.
Company building is an art form, but it is a group project. Beautiful work only arises when we care for our co-creators.
How we might work together…
Are you interested in launching your own consulting or service business or need help taking your current services business to the next level? Fleet is our holding company for services, and we’re actively looking to build business partnerships with winning leaders. Let’s talk!
My team and I lead Hearty, a boutique recruiting service that helps tech-forward companies hire proven talent. Our senior team of operators sources and screens, saving you time and money. When you need help, let’s chat.
Need help with a software project? Perhaps a product MVP, a project that requires outside help, or a fractional CTO for key strategic decisions? Our team at Shipwright Studio has worked together to build multiple successful startups, and we love helping leaders turn their dreams into reality. We're the team our clients trust for software built to last.
Looking for Influencer Marketing and Content Creation? The team from our previous company is back by popular demand with A2 Influence. We’re ramping up now and would love to share more.
Feel free to schedule a time during my Office Hours to discuss questions, feedback, networking, or any other topic!
BONUS: Cool Content of the Week
A little something I found meaningful. You might agree…
Scaling companies make people feel small
A tip of the hat to my friend and branding master, Leonora Polonsky, who turned me on to the strategy brilliance of Roger Martin. He recently wrote “The Downside of Scaling,” which lays out how companies that scale up tend to screw up the people side of things:
“As they scale, companies make their people feel small by the way they exploit three managerial devices: standardization, compartmentalization, and subordination.”
We leaders need to be nuanced—again, a lot like artists. Process, standardization, and levels of hierarchy are required to grow effectively. But we can look for ways to preserve the humanity in our work. With this in mind, we can build better.