🥁 The OffBeat #71: Riffing on What I've Learned From My Best and Worst Bosses

Leadership learnings from two decades of corporate work

This is The OffBeat, from jazz drummer, two-decade marketing leader, and mom of two Allison Stadd: music-inspired answers for your leadership challenges, like music-inspired rules to thrive at work.

“Disciplined imagination.”

That’s the paradoxical phrase jazz pianist and professor Frank J. Barrett coined in his book Yes to the Mess to describe how jazz musicians cultivate the ability to improvise.

The defining hallmark of jazz is improvisation: spontaneous creativity born of years of learning and craft-honing.

Good improvisers combine impromptu creativity with technical conviction.

As Mark Twain put it, “It usually takes more than three weeks to prepare a good impromptu speech.”

One of the jazz improviser’s tools is the riff, or a short musical phrase built for repetition. Riffs—also called licks—are reliable building blocks for improvisation; when combined Lego-like with one another, they make something fresh and appealing.

In the workplace, every leader you work for—if you use your over-listening skills—can kindle your individualized approach to leadership through riffs. You can inherit the riffs you can’t get out of your head, combine them with others in your junk collection, and in so doing continue to hone your own leadership style.

You can also consider riffs—leadership learnings—that sound discordant to you and modify the phrasing so they groove better to your ear.

Below are some of the leadership riffs I’ve collected from my best and worst bosses over almost two decades of corporate work.

Give up on knowing everything

One of my favorite bosses gave me guidance I’ve never forgotten: while I was onboarding into a complex role with a vast, global remit, he told me to give up on ever getting completely up-to-speed.

Instead, I should select the most critical topics to become an expert in and accept that I’d only ever have a surface-level familiarity with everything else. The “everything else” is what you rely on your team and your colleagues for.

Your team member’s promotion is a positive reflection on you, not a threat

As a senior manager at one of my first jobs, I told my CEO in a moment of inspiration that I wanted to be a VP on his team one day. We had an energizing conversation, and he had me write my commitment down on a post-it and put it in his office drawer for posterity.

The next day, my boss (the VP) called an impromptu 1-1 with me to say he felt uncomfortable that I had shared my ambition with the CEO, his boss; he said the VP job was his role, and asked me how I could (read: dare) therefore express a desire for that job.

The blatant tamping-down of my ambition—timed with my first experience managing a multi-person team—led to an existential reflection on leadership. I began to do the work to think overtly about my own leadership principles and philosophy. What sort of team did I want to nurture and lead, and how did I want people to feel when they worked for me?

Suffice to say, a core element of the leadership philosophy I’ve cultivated is celebrating and championing people’s ambition. When someone on your team soars, it’s a flattering reflection of your leadership, not a signal of your inferiority.

In fact, in Danny Meyer and Randy Garutti’s interview with Fortune this past June on Randy stepping down and selecting a Shake Shack CEO successor, they discuss how one of the greatest marks of leadership is how many great leaders that person themself produces.

Ideas first, scale later

Spending my formative professional years in fast-growing startups, each one hurtling toward IPO like a heat-seeking-missile, led me to approach marketing like an idea factory. Output quality and volume matter, but raw creative material is the reason the factory even exists.

A boss during these years taught me this: when ideas are in the germination stage, don’t bother contemplating how you’ll scale them. If something performs, you’ll deal with that later. Or you won’t, but you still learned something valuable to apply in another way.

Everyone’s time is valuable, regardless of level

One of my professional pet peeves is needing to follow up with people. (It’s why the first principle in my three-principle leadership philosophy is accountability; ACE = Accountability, Communication, Empathy. Do what you say you’re going to do, when you said you were going to do it.)

I always say a fairy dies every time you need to send a follow-up message.

Even more frustrating is when a leader insists on granular sign-off rights but is impossible to get in touch with(!!). Micromanagement and flakiness are poor bedfellows.

The same frustration extends to leaders who habitually start and end meetings late, cancel extremely last-minute, or ghost. There’s a general sense in these behaviors of lack of respect for people’s time. Yes, an hour of a senior leader’s time costs the company more in dollars than a junior employee’s does in terms of that finite unit of measure; but when you contemplate the long-term resentment and frustration the disrespect of time can foster in people, the math may not be that simple. Everyone’s busy, everyone’s juggling a million responsibilities inside and outside work, and it’s all material to the business in the end.

Consistency and clarity create security

A leader I loved would always say if you’re sick of hearing yourself repeat something to your team, then you’ve finally said it enough times (but keep saying it).

Everyone is dealing with an onslaught of information all day, every day, making it harder than ever for the critical tidbits to catch in the sieve of their brain. The more consistent your message, the more likely people will remember it and the more authority you’ll exude.

By the same token, my #1 learning from the toughest cultural environment I’ve encountered thus far in my career was to push your work and your team’s work to be as crystal clear as humanly possible. Wring your decks, talk tracks, and even your emails and Slack messages of every last drop of ambiguity. It leads to swifter comprehension, which means more efficient work. Clear, or simple, is HARD—and worth it.

Both consistency and clarity engender a sense of security. People at work crave boundaries and stability, within reason. Even (especially) in hectic, high-volume, fast-moving cultures like growth-mode companies, people can totally thrive in ambiguity and constant change BUT, in my experience, they require a stable foundation beneath them laid by a grounded leader. Even the most pliable bridges need deep-rooted stakes.

Confidence breeds trust

Everyone—quite literally everyone—deals with or has dealt with impostor syndrome. But showing up as an insecure leader can shake your team’s fidelity.

I’m not talking about being vulnerable or authentic; those are admirable leadership traits. I’m talking about letting your lack of trust in yourself leak out and contaminate your team atmosphere. If you can’t be decisive, or make the hard calls, or defend your team’s work publicly, how can you expect your colleagues to respect you?

A few of my former leaders’ lack of self-confidence showed up as micromanagement; in others, as weakness in situations that called for guts. Either way, their lack of self-belief sowed doubt in me that was hard to shake.

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Growth mindset is one of my three core values—alongside human connection and creativity—so learning from my own bosses, good and bad, is instinctual. It all goes into my leadership junk collection.

What have you learned from your best and worst bosses? I’d love to hear.

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Have a great week,

Allison

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