How Bad Managers Made Me a Better Leader
It may seem counterintuitive to attribute leadership success to the wrong-doings of previous bad managers, but sometimes the mistakes of others can be as valuable a teaching tool as learning the “right” way.
When you’re subjected to poor management it’s natural to have the naive response of, “When I’m in charge, I’ll do it differently!” But the truth is:
You’re more likely to make the same mistakes, mimicking the “model that you know,” or overcompensate in the opposite direction, then to magically hit the sweet spot right out the gate.
I should know. I did both.
But I’m here to tell you there is hope. You don’t have to be subject to the patterns of your past. The first time I got some challenging feedback about my early management style, I saw that I had fallen into an unconscious trap. And in that moment, a tsunami-sized wave of empathy for my past “bad” bosses washed over me.
Suddenly I got it. I understood their fear, the ‘losing control over the product’ anxiety, and the overwhelming dread from the nebulous ‘define your value through soft skills’ feeling that had left them stranded on the shores of leadership.
However, unlike some of them, I wanted to change. I saw how breaking out of those inherited patterns would help my employees, create a better work environment, and infuse my role with purpose.
Lesson #1: Start with Heart
Get to know your people first. Like, really. Yes, you all have projects to do, but don’t discount the importance of starting with a solid foundation of trust and a relationship with each member of your team.
“Bad” Boss Moment: On my last day at a company my boss said he wanted to send out the final announcement. In his farewell note he botched how long I’d been at the company (by over a year), what projects I’d worked on, and even misspoke about my interests (said I was a dancer, which anyone who knows me can confirm: I. Am. Not.). Embarrassing in the long run for him, but for me it solidified how little my boss knew me or my work, and further validated my choice to leave.
I also remember the first time I had a boss who asked me what was important to me. After rattling off a bunch of corporate buzzwords, he stopped me and said, “No, what is really important to you.”
I was confused. Almost every boss I’d had only cared about what I could deliver, when I could deliver it by, and not much else. He then told me how after some recent scares, his health had become paramount to him. In fact, as he was creating his annual goals with his boss he’d put “running a half-marathon” as a personal goal.
He explained how his boss was supporting all of his goals, not just the ones based on business ROI.
At the time I had recently returned to work after the birth of my daughter, and wanted to create a daily hard-stop for myself at 4:30PM to ensure I could spend time with her before her bedtime. Together we wove my family goals into my overall annual goals, and I felt supported in a profound new way.
Look beyond your bottom line
Of course work needs to get done, and it will, but I believe if you take the time to get to know the people on your team, you are creating a better working environment for them to thrive. Whenever I work with my team on crafting their annual goals, I ensure some goals are personal and tied to their core values, not just what they are committing to bringing to the company.
Lesson #2: Learn to deliver critical feedback
A short time ago I was watching Kim Scott give a talk on Radical Candor, and the moment that struck me was when she described, in the aftermath of laying off a ‘nice guy not cutting it,’ his confused lament:
“Why didn’t anyone tell me?”
One of the biggest injuries a “nice” manager can inflict on their team is not learning how to deliver critical feedback.
“Bad” Boss Moment: I once had a senior director confess to his leadership team that his biggest fear was having to tell someone “bad news” and to give them critical feedback. He’d even ‘managed people out’ rather than coach them through a teachable moment. While it is shocking someone could be in a high-ranking position and still not have mastery in this domain, he is not alone. In fact, I’d wager he has a great deal of company.
Delivering critical feedback is difficult, there is an art to it, and more models then you can shake a stick at: SBI, GROW, Radical Candor, three strengths and three opportunities, and so on.
To be honest, the model you should use is the one you will actually use. Regularly. Don’t just dust it off twice a year for mid-year or year-end-reviews. Learn how to give feedback early and often.
Visualize yourself on their side
One way I work to mitigate my anxiety around giving critical feedback is to picture myself sitting on the same side as the individual receiving the feedback. It can be a great mental pre-frame for your delivery. I also say to myself:
“I am committed to giving this feedback because I care and want them to succeed.”
Critical feedback isn’t about making someone feel bad about themselves; it’s about giving someone the tools to have the career they want, as well as helping them understand if they’re on the right path to get there.
One of the best “critical” feedback sessions I‘ve had was with someone whom I discovered was fundamentally unhappy doing in-house design. He was constantly frustrated with creating a MVP of his designs, and after a series of talks, I asked him to consider what his ideal environment would be as a designer. I suggested that an agency might be a better fit. After mulling things over, he chose to leave, and thanked me for my guidance. In the end both he and the team he left — who struggled with his constant moodiness — were happier because of it.
Lesson #3: Lead with Inquiry
This seems easy enough, but one of the biggest missteps I see with new managers is that they have not learned how to ‘lean-out,’ and provide feedback in ways that empowers their team.
“Bad” Boss Moment: I was in a stakeholder review and my boss shredded my work with a series of cutting comments. While some feedback was valid, most of it was misinformed because she didn’t have the full context on the project. However, rather than ask me questions about my choices, she went straight to prescriptive feedback. The way she did it gave me little opportunity to get what I actually needed from the review session, nor helped me grow by helping me uncover any gaps in my thinking. I left the meeting feeling publicly embarrassed and one step closer to leaving the company.
While it can take twice as long using an inquiry method to deliver feedback to someone, the long-term impact can create a higher performing and more committed team.
The key is to balance the growth of the individual with the timetable in the project, and know when to lean-in (especially with more junior level members on your team) so they know they do have a safety net. And for those times you do need to jump in, how can you turn those into teachable moments, instead of developing a “rescuer” habit.
The truth is being a “good” manager is incredibly challenging and finding your way is rife with pitfalls, missteps, and errors in judgement.
Most of us have our own “bad” boss moments.
Your job is simply to learn from your mistakes and course correct as you go. Also keep an eye out for the behaviors of the managers around you that inspire you, and think about adopting their behaviors to your own style. Keep your awareness up, your eyes on the horizon, and together we’ll make work a better place to be.
Below is a short collection of books I’ve read (or at least skimmed) and used in developing my own management style. YMMV:
The First 90 Days: A classic read on stepping into a new leadership role, how to assess your new environment, and create an initial action plan.
Lead Right: A crisp short read I like to give new managers with some basic “dos and don’ts” now that you’ve donned a manager mantle.
Multipliers: This book outlines common “well-intentioned” mistakes made by leaders that thwart them in building high-performance teams.
Playing Big: Tara Mohr’s fantastic book on helping women cultivate the tools to live a bolder life.
Radical Candor: Kim Scott’s popular two-by-two framework that breaks downs how to give direct, actionable feedback, from place of ‘caring deeply.’
