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What I Wish I Knew: Advice for Managing Managers

December 7, 2020
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As a first-time manager, you probably felt anxious about leadership and maybe even had imposter syndrome. Not only did you stay afloat, but you also succeeded — and now you’re on course to manage other managers. You’ll be setting strategy, helping other leaders grow, and advocating on behalf of a broader team.

While some of the skills you’ve already learned are transferable (like coaching), managing other managers requires a different approach. We asked senior leaders and coaches to share their advice for managers looking to take their careers to the next level.

1. Don’t mold managers. Empower them.

Think back to your first manager gig. If your boss was prone to micromanaging or asserting how they’d run your team, how did that make you feel?

Managing managers is all about trust. Instead of attempting to mold your reports into versions of yourself, experts encouraged deferring to their management style unless you absolutely need to make changes. “For any manager, including your reports, it’s critical not to become someone totally different than who you are. Having differing management styles within the same business can be beneficial,” said Deborah Sweeney, CEO of MyCorporation.

Don’t confuse this “hands-off” approach for apathy. While you’re there to support and coach managers, your most important job is making sure their direct reports trust them. According to the leaders we spoke to, the most consequential work tends to happen at the manager-individual contributor level — making those relationships incredibly valuable.

“Individual contributors having confidence in their managers is vital to your culture and how people are feeling,” said Teo Vanyo, founder of Stealth Agents. “You need to give managers space to make decisions and support their team. Build trust between you and the leader — and the leader [will build trust with] the individual contributors on their team.”

2. Evaluate managers on the big picture. 

When managing individual contributors, goalposts tend to be well defined. A sales or recruiting employee may be committed to meeting a quota or filling a certain number of open roles, respectively. But while employees’ targets should be specific and measurable, you have to evaluate managers through a broader lens.

“Metrics for success fundamentally change at the managing-managers level,” said Nicole Coustier, Executive Performance and Life Coach at Aurelian Coaching. “Previously, the success of the individuals that reported into the manager used to be the metric of success. But at the managing-managers level, you’re looking at the success of the entire initiative to assess performance.”

In practice, this means turning to goal-setting frameworks like objectives and key results (OKRs) to assess performance. You’ll use OKRs to evaluate manager performance on top-level outcomes, not tactical details. For a small client service team, accountability might look like:

Objective: Create a best-in-class customer experience. (Manager)
Key Result 1:
Improve client NPS by 20%  (IC)
Key Result 2:
Reduce average resolution time to 3 hours. (IC)
Key Result 3:
Conduct 100 interviews with churned customers. (IC)


In this case, you’ll need to assess the manager on the objective and team’s overall success, avoiding the temptation to single out key results. If an individual contributor fell short of a key result, defer to the manager to coach them. Only offer your support if they’d like guidance on how to approach those conversations.

3.  Workshop problems through coaching.

Constructive feedback between peers, direct reports, and managers should always be welcome. In practice, however, it’s often harder to give it to someone further up the chain. Middle managers are more likely to be subject matter experts, making it more likely that they’ll be defensive in performance conversations.

“Each manager you supervise will bring some kind of advanced knowledge. That may make it harder for you to question their methods without causing tension,” said Tony Giacobbe, Head of HR at Amica. Instead of coming in hot with prescriptive feedback, he recommended workshopping through potential opportunities during your one-on-one meetings. Offer yourself as a mentor and resource — instead of saying, “I think your team could have handled this better,” ask, “How can I help your team be more successful next time?”

If they haven’t already, directors and senior managers should brush up on the GROW coaching model, which revolves around asking questions like these. Among leadership experts, coaching came up repeatedly as the most valuable skill a “managers’ manager" can have.

“Your interactions with managers have to consist of 90% listening and 10% asking open-ended questions,” Vanyo said. “Managers don’t need to be managed. They need to be coached.”

4. Look before you leap. 

Managers, especially on smaller teams, are accustomed to juggling both strategic and tactical work. A recently promoted engineering manager’s duties may have changed, but they still have time to write code or troubleshoot issues. Leadership coaches say this juggling act usually isn’t tenable once you start supervising other leaders.

“Managers of managers need to actually like managing,” Coustier said. By now, you’re responsible for multiple teams, not just a few individuals. If you prefer being a player-coach, take stock of what you want out of your career. Not because one path is inherently better than the other, but because you owe it to yourself to be in a role that makes you happy.

“At this level, management activities will take up 100% of their time. So if someone prefers the more technical work that they started out doing, then they will not see as much success as others who genuinely like overseeing initiatives, removing roadblocks, and coaching other people,” she said.



Making the winding journey from middle manager to C-level executive isn’t about having a superhuman knack for knowing what everyone is working on. It also isn’t about having all the right answers. Not providing any answers might even be a strategy for success.

“This is a whole new game. Your job is to push people into thinking, and not thinking for them. You just won't have enough headspace to get into the nitty-gritty of things,” said Will Ward, CEO at Translation Equipment HQ. “The less they need you, the better you're doing your job.”

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