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From Boss to Coach: Best Practices from 15 Management Experts

Advice from leaders at Twitter, Square, Slack, Twitch (and more!) on how to coach your team to deliver outstanding results.

By Fellow.app  •   December 6, 2020  •   6 min read

Traditionally, managers have held a role commonly described as “command and control” – but that leadership model doesn’t work for today’s workforce.

According to Gallup’s recent book, It’s the Manager, Millenials and Generation Z want leaders who can coach them, provide regular feedback, and help them build their strengths.

“While the world’s workplace has been going through extraordinary historical change, the practice of management has been stuck in time for more than 30 years,” say Jim Clifton and Jim Harter. “The new workforce wants their work to have deep mission and purpose, and they don’t want old-style command-and-control bosses. They want coaches who inspire them, communicate with them frequently and develop their strengths.”

To support you in the transition from boss to coach, we asked a panel of experts for their most valuable tips and advice for managers. Keep scrolling to read what our panelists had to say about the following five questions:

1 How can managers help employees develop professionally?

“As a manager, I like to know what each of my employees are aiming for long-term. That way I can open up opportunities and encourage skill growth that will help lead them to where they want to be. I don’t make their growth choices for them, instead I listen to their dreams.”

– Marissa Goldberg, Founder of Remote Work Prep

“I’m a big believer in making sure everyone feels like they have ownership somewhere. Contributing is good, but let people have an area they can make decisions in. If you set goals early, it allows you to frame honest feedback within those goals – that way what you’re saying is always aligned with getting the team member the best shot at where they want to go.”

– Jack Appleby, Sr. Creative Strategist at Twitch

“As a manager, my core job is to help identify and resolve any blockers that folks who I work with have. I consider myself a coach to them which enables me to adjust my approach based on each individual person and their responsibilities in the company. A useful approach to helping a direct report with career progression is to assist them in setting short, mid and long-term goals. By explicitly defining these goals, career progression becomes measurable and can be monitored at a regular cadence during 1:1s.”

– Hiten Shah, Co-Founder & CEO of FYI 

2 Should leaders integrate career conversations into their one-on-one meetings?

“I’m not a fan of integrating it into the weekly 1:1. I prefer to have a specific time 1x a month to check in on career. In a 1:1, you can run out of time. Having a dedicated moment to have the conversation also indicates that their career goals are important.”

– Elizabeth Kinsey, Senior Marketing Manager at Slack

“I have a skills/engagement framework I use to evaluate how people are doing. The prescription for high skill and low engagement is lots of questions and *actually* listening. It’s important for me to write things down. Last piece is to review previous notes and follow up.”

– Jordan Skole, Director of Product Growth at Autobooks

“I’ve found success in making dedicated, monthly, hour-long sessions dedicated to career conversations. While you should be talking about how to push forward their career aspirations in every one on one, it’s much easier to have a substantial conversation when you both have set aside dedicated time to think about progress made since last time, specific action items to take, and frank evaluation of how they’re doing.”

– Kathryn Gonzalez, Head of Design Infrastructure at DoorDash

3 How can managers become better listeners?

“Stop yourself from answering direct reports’ questions right away. Your team will often come to you with an issue or question, expecting you have answers. Create opportunities for them to reveal their ideas and suggestions before you problem solve.”

– Michelle Kim, Co-Founder & CEO at Awaken

“Ask ‘why’ a lot more. Or its less aggressive cousin, ‘What was your reasoning behind doing it this way?’ If you focus on the actions being done and understanding why they are done, you might uncover the problem that’s causing the problem.”

– Stefan Palios, Founder of Remotely Inclined

“Focus on building a feedback-first culture, where it’s normal and encouraged to regularly share constructive and positive feedback. With this foundation, your team will feel comfortable voicing problems proactively.”

– Phil Jacobson, VP Product & Operations at #paid

4 What steps can leaders take to uncover their teammate’s individual motivations?

“Ask them. In previous roles, what were the factors that led you to a win? What do you enjoy about your job? How do you like to be managed? What demotivates you? The failure of most relationships is the communication gap.”

– Mallory Greene, CEO at Eirene Cremations

“I’ve always done this through open conversations and relationship development. The more you are invested in your team, they more they will trust you and open up about what they want.”

– Kelly Rusk, Marketing Communications Consultant

“It sounds simple, but I ask what do you want? What makes you (and keeps you) motivated? I do this because it’s often not about money. It might be about flexibility, responsibility or the work. What makes someone motivated is personal.”

– Meg Button, CEO & Co-Founder, Nuscreen Inc. 

5 What are some best practices to provide performance feedback in a way that’s helpful and fosters growth?

“Like coach Taylor, be firm but fair. Direct but not demeaning. Always respectful. And I’d encourage a follow-up discussion as not everyone (myself included) can digest all this in one discussion. Like compensation, conversations on career performance and expectations aren’t easy. I like to be transparent about this to break the heaviness of it all. In addition, using a shared doc that we can both reference hold ourselves accountable has been helpful.”

– Dave Brown, Design Director at Square

“In order for constructive feedback to be effective, it has to be specific, timely, and completely objective. NEVER criticize the person, criticize the behaviour and why it needs to change. Then shut up and let your employee absorb.”

– John Fleischauer, Chief Talent Officer at Pivot + Edge

“I think feedback should be clear, direct, and actionable. Compliment sandwiches can make the person unaware you expect changes. But if the feedback may be hard to hear, it must be done in private and when the person is expecting feedback. No hallway blindsides.”

– Joe Wadlington, Global Creative Lead at Twitter

Closing advice

In a recent interview with Forbes, Jim Clifton (Chairman and CEO of Gallup) and Jim Harter (Chief Scientist, Workplace at Gallup) shared the following three tips to make the transition from boss to coach:

  • Know yourself: Cultivating strong self-awareness is key to effective management.
  • Know your employees’ strengths: Instead of focusing on employee weaknesses, try to understand each person’s “superpowers” and give them tasks and responsibilities to help them build on those strengths.
  • Understand the difference between coachable and innate traits: Understand what behaviours and patterns are “coachable” for each employee.

As a manager, it’s one of your main responsibilities to encourage growth and confidence in your employees.

We hope that these expert tips will help you build an environment where employees feel engaged, supported, and motivated to do their best work.

If you’d like to participate in live Q&As like this one in the future, make sure to RSVP for our next #ManagerChats!

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