After a decade of climbing the ranks at Google, I reached the point of managing other managers. Despite the company’s apparent confidence in me, I struggled with performance anxiety. A decade in the trenches didn’t guarantee my potential for upper management. Could I deliver at the same level with significantly more people in my org?

A flight to Boulder early in my tenure as a senior leader left me with a few hours of peace before leading an off-site the next day with a number of the managers who reported to me. We would spend a day planning a high-stakes transition, shutting down a major business unit in one part of the country and building it back up in another. With my impostor syndrome flaring, I used every trick in the book to wrangle my uncomfortable emotions and face the blank page I’d just opened with a clear head.

For the duration of the flight, I worked on the strategy we were supposed to develop the next day: our North Star mission statement, the three pillars of the transition, a leader for each one and so on. As I resolved each area of uncertainty, my anxiety subsided and my confidence grew. Yes. This is what the team needs.

This is how I will prove my value to the organization. This is Jenny Wood as boss.

I didn’t get much sleep that night, as there was still too much prep to complete. However, by the following morning, I’d completed an elaborate, 30-slide deck outlining how the transition would work. Once I finished, I wondered whether we still needed the full day. I’d resolved every open question. You can thank me later, folks. When we assembled in the conference room, I plugged my laptop in and opened the first slide, crammed with answers to the problems we were supposed to solve that day. Ta-da!

To my surprise, the energy in the room immediately changed. It got so quiet you could hear an erasable marker drop. However, I assumed they were busy absorbing the extraordinary quantity of leadership I’d stuffed into a single slide, so I started presenting. Once I finished blowing their minds, I smiled triumphantly and opened it up for questions.

They raked me over the coals.

I quickly learned that the whole presentation had been an insulting affront to the team. The comments went something like this: ‘Why would you come here thinking you have all the answers?’ one manager essentially asked me. ‘We were coming together as a team to tackle this problem. We bring a combined 35 years of experience to the table. How long have you been in this role, three months? Who are you to say that one of us should lead the people pillar and another should lead operations? Do you even know our strengths yet?’ That was the gist.

By the time everyone had said their piece, I was mortified. That said, I knew what I had to do next. “OK, team,” I said. “My apologies. Let’s scrap this plan and start over.” This was the beginning of the most difficult transition of my career. My approach at that meeting encapsulates the dark side of ‘bossiness,’ where insecurities run rampant. All I’d needed to do was toss a bunch of Sharpies on the table, ask some open-ended questions and encourage people to contribute. Creating a safe ideation would have made it easier for them to bring their valuable experience, expertise and talent to solving the problem.

The point of a manager or leader is to bring out the best in the team. To make their jobs easier. It can feel uncomfortable for new bosses, but getting others to do the work makes you look much more effective than struggling to do everything yourself.

As an executive at Google, I learned to leverage my team’s knowledge and abilities, delegate to them wherever possible and attempt to spend more of my time listening. My leadership experience couldn’t have been more different from my work as an individual contributor. That’s because, unlike individual contributors, leaders aren’t expected to bring answers. They’re supposed to ask questions:

• What does the company’s vision mean for our team?
• How will we execute against our mission?
• What are the key metrics to watch?
• What strengths do we bring to the table?
• What will make this meeting successful?

Your questions may differ, but the approach is universal. Leaders help others succeed. As a leader, are you ready to stop inflating your ego and start lifting others instead?

In defence of bossiness

When I say ‘get bossy,’ I mean be a genuine boss: an empathic, supportive, yet decisive leader who knows when to speak up and when to listen, when to let the team figure a problem out themselves, and when to step in with help and a fresh perspective.

Something happens when you keep successfully getting what you go after. People look to you for guidance. They set their bar by yours. Unfortunately, some people use the power they gain for personal ends. The shift towards self-interest spells an early end to their reign. On the other hand, leaders with longevity double down on the generosity that got them where they are:

‘How can I support you this week?’ caps every weekly one-on-one with a direct report. They set up office hours for employees to share ideas and ask questions. They delegate everything they can, refusing the temptation to make themselves indispensable. They praise publicly and admonish in private. Ultimately, leaders like these serve others even more than they did on their way up the ladder.

When I first rose to a leadership position, I experienced impostor syndrome, exacerbated by my mistaken belief that I needed to know, see and do all. Then I learned I was there to help my team solve problems instead of solving problems for them.

Here are a few key principles I’ve learned about being bossy in the best sense of the word.

Principle 1: Hands off the wheel.

You lead by helping others do their jobs more effectively instead of doing the job yourself, but it’s hard to relinquish control. I became a leader at Google because of my ‘fancy driving.’ Now, I was supposed to let others take the wheel? I fought the idea stubbornly until a boss defused my resistance: ‘You get full credit for everything your team does.’ Wow.

Since my promotion, I’d struggled to reconcile the desire to be seen as successful with the responsibility to help others shine. Though I understood leadership intellectually, part of me had held back, reserving the right to dive in and fix things when my team did anything differently than I would. In short, I had the whole thing backward. It wasn’t either-or. It was both.

This meant letting go of the wheel. Doing the day-to-day work deserved only half my attention. The other half? Communicating up, down and across:

Up: Sharing our accomplishments with leadership.

Down: Helping my team understand the larger vision driving our specific goals.

Across: E-mailing stakeholders and peers across the organization ensuring seamless integration of left and right hands.

If I coach my team to success, I’m the coach of a winning team. That’s a good thing. Watch any football game, and you’ll see that those potbellied old coots on the sidelines are as excited as the players after a victory. They get paid for winning seasons, not scoring touchdowns. Now that I was a sideline geezer, it was time to put down the ball and pick up the whistle.

As a leader, you’re seen as a winner if you lead a team of winners. So forget about taking credit. Delegate. Bestow credit wherever it belongs. Celebrate your team’s successes with the rest of the organization. Advocate for them. Name names. Turn your direct reports into heroes.

In your first management role, suddenly making yourself dispensable in this way feels terrifying. Until you lead a team, you succeed by convincing everyone that you are essential to getting results. The organization needs you to do X, Y or Z. Your ability to deliver persuaded them to put you in charge of a team. Now the game changes, however. Leaders are judged by a different metric: the ability to generate seven times as much X, Y and Z from others.

If you’re uncomfortable building relationships and influencing others, stick to being an individual contributor. If you enjoy doing the work, you won’t be satisfied helping others do the work better. You’ll be in meetings or on calls. If connecting with others isn’t your happy place, find ways to gain seniority and more pay without entering management. Because leaders lead. They set objectives, rally the troops and ensure steady progress towards the goal.

Principle 2: Patterns, not problems

Putting out fires all the time leaves no bandwidth to notice, let alone address, that the building itself is a tinderbox. Rather than get to the root of things, managers scurry from one thing to the next, cleaning things up, cursing their bad luck and wondering why their leadership isn’t more effective.

“I solve for patterns, not problems,” my colleague Jen McGann once told me. This is what great leaders do. While the team solves individual problems, they step back from the trees and observe the forest. I’m sure you’re nodding along. Pattern-seeking makes sense in theory, and nearly any leader will claim they prefer that approach. However, the practice of actually seeking patterns remains murky.

As leaders, we like sober judgment and deliberate strategy as concepts but often struggle to make the leap from problem solver to pattern spotter. Sticking to a step-by-step process will help turn an abstract notion into a daily habit.

Consider the following example: At the quarterly roundtable with the VP and some individual contributors, a sales rep announces that customers are complaining about the new red widgets. Apparently, some find them much harder to install than the old green ones.

“We don’t want unhappy customers,” the VP knee-jerks. “Stop selling the red widgets. Let’s put all our energy into selling the green ones instead. Those have been around much longer, and no one ever complains about the installation process.” Problem solved. Or is it? Next time you’re tempted by the relief offered by a quick and easy fix to a pressing problem, QUASH it:

Quantify: Start with broad, quantitative data. In this case, pull a comprehensive report on all widget sales for the last several quarters or years.

Understand: Next, leverage your team. In roundtables or one-on-ones, talk to people with relevant knowledge and experience. In this case, bring together the member of your leadership team responsible for widget product design, the one in charge of quality assurance and the documentation lead. What’s going on with the red widgets? Did we expect feedback like this? What might be done to address it?

Assess: Once you have enough context, go directly to those involved. In this case, you or your team might contact the customer support representatives who have been fielding complaints about red widgets. Do the people buying them share demographic factors? Are there compounding factors that adversely affect these clients in particular? What about people who don’t have problems installing red widgets — what do they have in common?

Support: Once you’ve fully explored the problem and its possible root causes, you may already have a course of action in mind. Regardless of how you proceed, confirm with the original hand raiser that you have heard and understood the problem as they see it. If workers don’t see support for their concerns, they won’t bother raising their hands the next time they see a problem.

Hypothesize: Doing nothing is underrated. In many cases, employees exaggerate problems. Not deliberately, but because they have a narrower view of the picture. A disproportionate response to a relatively minor issue can cause more trouble than it resolves. Sometimes, a clear picture emerges only after more time passes and more data is gathered.

Transitioning from problems to patterns is tricky for those new to authority because, until we’re in charge, we’re rewarded for solving problems quickly and efficiently. That makes us want to be seen as solving problems quickly and efficiently. Solving a problem directly instead of helping the team solve the pattern is performative work for leaders. You must multiply the impact you made as an individual contributor. That’s why you have a team! Once again, a behaviour that served us well in one stage of our careers has become a disadvantage in another.

Principle 3: Fail-safe feedback

As we’ve seen, being bossy involves more understanding and helping than deciding and ordering. One of the most important forms of help you can offer is feedback. You’ll discover that top performers crave feedback. If you have a talented team that operates at a high level, chances are they possess a robust growth mindset. On the other hand, for those less skilled or motivated, you owe it to them to share how they level up. Performance doesn’t improve through osmosis. Where top performers crave feedback, bottom performers need it.

We all have areas for improvement, and no one is better placed to identify and address those areas than the team’s leader. When you spot a rough edge, give that employee the information they need to sand it down. Just don’t overdo it.

In my first few years as a manager, I gave feedback on nearly everything my direct reports did. If you showed me a 20-slide deck, you’d get at least three or four comments per slide. This was my insecurity rearing its head. I wanted to show them I was invested, but I overwhelmed them instead. I learned to focus on a handful of macro issues and ignore the micro stuff. Otherwise, I would have stopped adding value and started draining morale.

Aim for a five-to-one ratio: five positives for every negative. The positives can be anything: a high five here, a “great job on that report” there. Even the occasional happy-face emoji. A single negative comment can be crushing unless it’s cushioned by plenty of positive ones.

Giving constructive feedback can be a minefield, depending on the organization’s culture and the vibe you’ve established with your team. Next time, stay SAFE:

Setting: Instead of offering feedback in general, address a recent instance of the problematic behaviour and say when and where it happened: “Let’s talk about your presentation at last week’s partner meeting.” Be specific even if the behaviour happens frequently.

Action: Describe the behaviour in simple and concrete terms without editorializing or catastrophizing what happened: “You talked over senior leaders three times.”

Feeling: Once you’ve identified the problem, seek to understand the other person’s intention before going further: “What were you feeling when this was happening?” This gives them a chance to say, “Oh, wow. My intention was not at all to talk over them. I was anxious that we wouldn’t get to the end of the presentation, which covered the data the senior leaders had specifically requested.”

Effect: Acknowledge their intention yet explain the negative outcome of the behaviour: “Ah, that makes sense. You were nervous about not getting to the analysis; however, cutting people off this way made you seem impatient and less collaborative than I know you are.”  From there, brainstorm simple ways to improve. For example, someone with the bad habit of talking over others — including yours truly — might count to three after anyone else stops talking before continuing. It’s a solvable problem.

Specificity and objectivity are crucial. We all learn differently, and many of us struggle to absorb or act on abstract feedback. For example, telling someone they “always talk over others” may frustrate or confuse them. After all, every conversation has an ebb and flow, and it’s natural to experience some overlap. By drilling down to a specific instance, you cut past what happened and focus on the disconnect between the person’s intentions and the real-world outcome.

You can also instill in your team a practice of “one up, one OPP.” Whenever someone presents or delivers a project, you share one thing they did well (up) and one opportunity for improvement (OPP). This builds the muscle of giving feedback, keeps it light and avoids overwhelm. It’s a forcing function for giving feedback immediately instead of waiting for the next performance review.

For example, when leaving a client presentation: Your one up is that you used more hard data in your slides this time — it was compelling. Your one OPP is that you should avoid using “you know” as filler language.

SAFE feedback gives the other person everything they need to improve. You’re telling them exactly what they did and why that wasn’t the right approach. And if they have several material areas of development and don’t improve after being given ample chances, be BRUTAL and let them go. Don’t sit on it. You know where this is going.

Principle 4: Don’t break people

“People who worked on 30 Rock all moved away as fast as they could when it was over,” Tina Fey, reflecting on her leadership as an executive producer, told Conan O’Brien on his podcast, “because I think we broke them. I think we broke a lot of people. It was a loving staff, and there was a lot of pride, and we did a lot of good work, but I think a lot of people never want to see us again.”

If we’re obsessed, we expect those on our team to be as committed and hardworking as we were in their position. Your work ethic is always transparent to you. The efforts of your direct reports are often opaque. If you expect the people on your team to look as busy and hardworking on the outside as you feel on the inside, you will be disappointed and frustrated. These mis-calibrated expectations will come out in the form of unrealistic quotas, hallucinatory milestones or a wildly unbalanced feedback-praise ratio.

Principle 5: Don’t be toxic

The word toxic gets thrown around liberally. If you want to be a better manager, it helps to ground your understanding of toxic leadership in real life behaviours. Here are a few common variations:

Urgency and anger: By default, make most things you ask of your team a minimum five-business-day turnaround. Unless you’re running a hospital, you’re not saving lives. It’s your job to plan ahead instead of running things with a constant degree of urgency. Give people ample time to prepare — and reserve the fire drills for when you smell something burning. Likewise, never use bold text, all caps, exclamation points or any other form of emphasis in communicating with your team unless it’s positive. There is an imbalance of power. As a manager, every whisper is a shout.

Envy and credit-stealing: As discussed, there is no need to worry about credit where your team is involved. When they win, you win. Hire people smarter than you, help them succeed and then get out of their way. Let them know that your job is to coach them to be better than they think they can be. That’s the real magic. You’ll find that the only thing more valuable to an organization than being a top performer is being someone who can hire, lead and, most important, retain top performers.

Indecisiveness: The team looks to you for guidance. Don’t waste 45 minutes of an hour-long meeting trying to collectively arrive at the right coverage plan for Troy’s paternity leave. (I’ve done things like this, and in each case, my team very much wished I hadn’t.) Listening and collaboration matter, but you must decide. If your title is “director,” direct. Don’t hem and haw, don’t try to please everyone on small decisions, and don’t go back and forth once you have decided. Be brutal about what is most important.

To lead, you need it all: curiosity, obsession and the willingness to influence others. You must create so much benefit for others that people are drawn to join you in your quest. Find and cultivate allies, partners and collaborators, and be bossy: Help your people aggressively and push them constantly. Michael Jordan relentlessly needled his teammates to do better. He simply wouldn’t let them underperform. Challenging as it was to play with him, in the end, they were all grateful. He made them champions.

This article is an excerpt from the book Wild Courage: Go After What You Want and Get It (Portfolio, 2025). It originally appeared in the Fall issue of the Rotman Management magazine.