This article is by Anita Hossain Choudhry and Mindy Zhang, who have coached hundreds of managers. Hossain Choudhry is CEO at The Grand, a group coaching platform to support managers in making leadership decisions. She’s also an executive coach (formerly at Reboot.io) and previously the Head of Knowledge at First Round Capital. Zhang is a former product leader at Dropbox and at Oscar Health, and is now an executive coach at Throughline and The Grand.
Think about your typical week as a manager. How many times did you help your direct reports by trying to solve their problem? The answer is probably as many times as you met with them. While that’s common among managers, it’s not always optimal.
Too often, managers feel the best way to add value is by fixing someone’s problem. “I know the answer, and I need to tell them,” we say to ourselves. But over-relying on fixing constrains our ability to lead and robs our team members of growth opportunities.
As a result, many managers get overwhelmed with responsibilities and burn out. They create a team culture in which they’re expected to have the answers. And their direct reports — instead of utilizing their talents and stretching their problem-solving skills — become dependent on their managers to do their jobs.
Managers are not solution vending machines. They’re not paid to give answers.
Great managers know they need to invest in the long game: building a team that is constantly growing, feels empowered to drive results, and reaches higher levels of performance.
In our experience, many managers stumble here because they lack the knowledge about what else to try. Especially in the startup setting, manager training is often inadequate (if it even exists). Most managers haven’t been taught how to assess their style or shift their approach — many bring the best of intentions, but frankly, simply end up winging it.
But if they aren’t aware of it, most managers default to a single approach. Daniel Goleman, a psychologist and leadership author, studied 3,871 executives and identified six leadership styles: Commanding, Visionary, Affiliative, Democratic, Pacesetting, and Coaching. What he found was that the most effective leaders didn’t over-rely on a single style; they had mastered multiple styles and could skillfully match the right style to a situation.
Similarly, as a manager, you have a toolbox of skills, styles, and competencies to pull from. In order to be the best manager possible, you need to: (a) assemble a diverse and varied toolbox, and (b) wisely select the tool that will be most useful in a given situation.
As executive coaches, we’ve worked with hundreds of startup managers. We’ve seen first-hand that coaching is one of the least utilized and yet most effective management tools. (In fact, in Goleman’s research, coaching was rated as leaders’ least preferred style, even though it correlates with positive team dynamics.) By adding coaching to your toolbox and calling upon it in the right situations, you can uncover your team’s blind spots, help your direct reports grow into more capable leaders, and ultimately, enable your team’s best work.
In this article, we’ll unpack why managers fall into the fixing trap and dig into the fundamentals of coaching, sharing four actionable tools you can start using immediately. We’ll distill the highlights of what we’ve learned in years of coaching training — all adapted to everyday management scenarios so you can see how to practically put them to use.
Picture this: You’ve just finished your morning coffee and call into a regularly scheduled 1:1 with a high-performing direct report. Before you’ve had time to chit chat and establish an agenda, they express frustration about their role:
“To be honest, I haven’t been feeling motivated at work. I tend to be bogged down in execution details, and I’m not getting enough exposure to strategy. I look around, and my peers are working on strategic projects that move their careers forward.”
How would you approach it? Most managers start scanning for problems. Once they’ve identified a problem, they jump straight to fixing it. Take this example of the manager (Rachel) and her direct report (Ana). If Rachel uses a fixing approach, here’s how that conversation might go:
What did you notice about the conversation above?
First, the manager started with advice from her own experience. She assumed that her direct report was asking for strategic opportunities in order to get promoted, and that sharing lessons from her own career advancement would be relevant. While those assumptions might be true, it’s also possible that her direct report has a different “why” behind the ask — for example, acquiring a new skill, gaining confidence, or charting the course for a different career path.
Second, the manager prescribed solutions — creating a competitive analysis slide, partnering with another colleague on a strategic project — before understanding the root cause of the problem. The manager and direct report engage in a frustrating game of ping pong. The manager suggests a solution, and the direct report counters it. Little progress is made. The manager exits the conversation thinking that their direct report is difficult, entitled, and not focused enough on their core role. The direct report leaves feeling unheard and dismissed.
We’ve encountered this very situation in our own careers. When Anita was managing several people who had just graduated from college, she reflected on her own first job — and was reminded of a manager who was unclear and didn’t offer the right level of support. Vowing to do the opposite, when a direct report came to her struggling to prioritize everything on her plate, Anita immediately jumped into fix-it mode, getting super prescriptive.
She told her to take a sheet of paper, draw a triangle on it, and then break it up into thirds. In the bottom of the triangle, Anita wrote down 3-5 things her report should work on for the week. Next, she outlined three things for the next three days in the middle section, and the one thing that she needed to complete before she left the office for the day at the top of the triangle. Anita did this for her direct report every day for several weeks, thinking she had solved her problem. Oftentimes, Anita would also look at that triangle and take a few things off of her plate and just do it for her, trying to lighten the load. Yet the direct report’s creativity started to wane as she spent long hours trying her best to get those critical tasks done.
Why managers are prone to fixing:
Situations like this are common in manager-report relationships. When a manager adopts a fixing approach, they assume that:
1. Their experiences are relevant to the other person’s situation.
2. They know the other person’s problem well enough to prescribe advice.
A fixing approach isn’t always bad. Sometimes, we do know the other person’s situation accurately, and our advice is tailored to their specific problem. But in many management situations, jumping straight to fixing causes (a) a misinformed solution that makes the problem worse, (b) a band-aid solution that temporarily soothes the wound but doesn’t solve the deeper issue, and/or (c) a long-term dependence on the manager to fix all problems, thereby depriving the direct report of opportunities to grow and solve their own challenges.
Why do managers instinctively dive into fixing? Two big reasons:
We think we know: We got promoted into managerial roles from senior individual contributor (IC) positions because we excelled at building our expertise and swiftly applying it to solve problems. We’re wired to think, “I know the answer and can add value here” and jump into action.
We think we should know: Many managers (particularly those who are new to managing people) experience imposter syndrome. They might think, “I should know the right answer. Otherwise, if I don’t, I’m a bad manager.” To protect our own credibility, we take on immense pressure to fix problems.
Being the hero who swoops in and relieves someone of their problems feels good, and it’s hard to let go of the chance to reinforce our competence.
Many have had brushes with that second one in particular. When Mindy became a people manager at Dropbox in her mid-20s, she battled imposter syndrome as she managed people with up to a decade more experience. Whenever a direct report came to her with a challenge, a negative talk track kicked in. She thought: “I need to solve this problem for them, now. Because if I don’t… Well, they’ll know that I’m faking it. That I’m not a real product leader.”
As a result, she often overworked herself solving team members’ problems, and most of the time, her solutions were misinformed because she didn’t have full context. A wake-up call came while working with an executive coach who did a round of in-depth 360 feedback that scored her across dimensions of leadership. “Keeping talented people challenged” was her lowest score. Mindy realized that the amazing product managers she was hiring were joining her team so that their strengths and expertise could shine, not so she could take on their problems.
In many management situations, coaching is the most effective approach. Coaching allows us to shift the focus away from ourselves and onto the person we’re coaching.
Of course, this term is still a bit fuzzy, especially in the startup world, where coaching can take many forms. We define coaching as getting someone from where they are to where they want to go by tapping into their own wisdom and keeping them accountable to achieving their goals.
To put it simply: Coaching is a skill, while being a manager is a role.
The key element is tapping into their own wisdom, not your wisdom. When we constantly support our teams using our wisdom, we are hyper-focused on solving the problem at hand based on our past experiences and learnings.
Returning to Anita’s own management example, an “aha” moment arrived during her first coaching certification course. One of the training sessions talked about how we often live our lives according to someone else’s compass. Only through deep inquiry and by asking open and honest questions can we know our own compass. Anita realized that by adopting a fix-it management approach, she was trying to get her direct report to use her compass to define success — and as a result, the employee was no longer connecting with the work that had her so excited in the beginning.
In their next 1:1, Anita instructed her direct report to take the lead filling out that triangle. To aid in the process, she asked open and honest questions about what type of work her team member was most drawn to and where she saw opportunities for the firm to grow. By taking a coaching stance, Anita helped her trust her intuition and develop her own compass. In turn, this allowed the direct report to come up with some of the most creative ideas deployed at the company, returning to the vibrant and innovative person Anita had hired in the first place.
When we instead use coaching to unearth someone’s own wisdom, two things happen:
We invest in their inner teacher: This means that you’re not just solving a one-time problem; you’re helping them see patterns and behaviors so that going forward, they can develop their own resources and best practices to navigate their challenges.
We empower them to trust themselves: You’ll see a shift in your team member’s ability to more clearly and confidently articulate next steps they can take to solve a problem or achieve their goal.
Coaching 101 = Empathetic listening + open and honest questions
Before sharing a few coaching tools, we want to dive into two foundational skills that are essential to start coaching your direct reports: Empathetic Listening and Open and Honest Questions
To highlight empathetic listening, we need to start by defining the opposite of empathetic listening, which is self-focused listening. We’ve all been there before. Whether it’s in a 1:1 with a direct report or a cross-functional meeting, we often listen to other people in order to answer one question: What does this mean for me?
We are listening to react and respond: What should I say next? What conclusion should I draw? How should I interpret this? What does this person need from me? How do I help them figure this out?
This is a natural human reaction because our brains are designed for pattern matching and problem solving — which can be quite useful in many parts of our lives. Instead, we recommend that managers use empathetic listening.