A lack of career growth opportunities is one of the leading reasons employees leave a job.
But what’s a manager to do to retain their team? Even the best managers are set up to fail sometimes.
Managers can’t magically manifest open headcount or guarantee immediate career progression, yet they are accountable for delivering against company goals and helping their direct reports grow.
These responsibilities, alongside managing their personal career ambitions, require entirely different skills, yet most lack proper training to succeed across the stack.
Especially in high-growth startup environments where ambiguity and constant change are the norms.
Unfortunately, a lopsided focus on just one of these responsibilities can lead to real consequences.
Managers often don’t support the growth of their reports because they are too focused on business tasks. As a result, they lead disempowered teams.
On the other side of the coin, managers too focused on individual development at the expense of delivering against company goals will be seen as ineffectual and soon be replaced.
To avoid over-indexing on either skill, managers need to develop a new one: coaching.
Coaching is the toolkit that helps employees see more options and make deliberate choices about what they want to do next — and it’s one of the highest leverage skills managers can build to navigate their varied responsibilities and retain employees more effectively.
Unfortunately, the tech industry has done very little to effectively train managers with this skill set.
I want to see that change.
In this piece, we will cover:
The definition of coaching and how it fits into a manager’s portfolio
Why most managers struggle to coach
We also created a new Coaching Reflection Template that you can use to instantly apply the coaching frameworks, tips, and ideas outlined in this article.
Meet The Author
Natalie Rothfels is an Operator in Residence at Reforge and runs a leadership coaching practice. She has held product leadership roles at Quizlet and Khan Academy and was a classroom teacher before that.
What is Coaching & Where Does it Fit in?
You might already be a good manager. You have a clear focus, your team is performing well, and you give timely valued feedback often.
Even so, it’s likely that you’re not really coaching.
Most managers think they’re coaching when they’re actually directing or evaluating.
Directing is clarifying the strategy, goals, and roles that are required for a team to reach an impactful outcome. Its primary purpose is to highlight responsibility by clarifying what success looks like and who owns which parts of the whole.
Evaluating is driving outcomes for the company. Its primary purpose is to be accountable for performance by organizing people, time, and resources effectively to hit a target goal. This includes giving feedback and providing training to upskill for effective execution.
Coaching is developing people to navigate successfully on their own. Its primary purpose is to drive development by helping someone learn and grow so they can achieve more of what they want in as effective a way as possible.
The promise of coaching is two-fold.
First, by becoming a more proficient coach, you’ll unlock real growth potential on your team. Access to professional development and advancement is now commonly cited as a huge driver of employee retention. The more your people grow, the more likely they are to stay.
Second, coaching provides you with high-fidelity information from your reports that will make directing and evaluating significantly easier. Knowing what motivates the individuals on your team can help you pick the right projects for them to own.
Coaching, directing, and evaluating make up the portfolio of people manager responsibilities. To get from good to great, you will need to embrace all three.
Let’s walk through an example to see how they fit together.
Imagine there’s an upcoming project to build a landing page, and Rebecca is overseeing the project’s success. She has three distinct roles for the project to succeed:
1. Coaching:
Helping team members be more effective at solving cross-functional dependencies
Helping individuals navigate their productivity against the goals
2. Directing:
Defining the goals/metrics for success
Defining the target audience
Clarifying what’s in-scope
Assigning who is going to work on it
3. Evaluating
Ensuring the requirements get met
Figuring out tactical roadblocks like budget, managing dependencies across teams, and more
Being accountable for the outcome
Jori, her report, comes to Rebecca to seek counsel because they’re struggling to get content from the marketing team in time for launch. It’s Rebecca’s job to figure out which course of action in this toolkit is most useful in that context.
If Rebecca took a pure directing approach, she could give Jori explicit directions of what to say or relay to the marketing counterpart. She might even go directly to the marketing counterpart and clarify a deadline so that Jori doesn’t have to.
If Rebecca took a pure evaluating approach, she might decide to share some feedback with Jori about why some of the efforts haven’t been successful so far. Perhaps, for example, Jori was never clear with the marketing team on important deadlines, or why they were so critical to hit. This has made it hard for the marketing team to prioritize the work effectively.
If Rebecca took a pure coaching approach, she may ask a handful of questions to understand what Jori has done to date and help to identify the biggest challenge that may require support. For example, is it about communicating with the marketing team effectively, or about prioritizing this versus other efforts?
Of course, Rebecca can also choose to combine these approaches.
She could start with some coaching questions to understand the context and then move to directing to guide a specific course of action depending on Jori’s competencies and capacity. After the project is over, Rebecca may then choose to share feedback or do a retrospective with Jori on what made the project frustrating or empowering at different points.
These types of situations can seem so straightforward, but they’re often complex and require different tools.
That’s why I’m a big advocate of viewing these three approaches as a portfolio.
Managers need to have all three at their disposal and know when to deploy each.
We’ve done a real disservice to managers by not training them across the stack. Early managers are much more proficient at directing because it’s usually their performance as individual contributors that lands them a managerial seat.
Senior managers know that performance matters above all. So they can become over-reliant on evaluating at the expense of clear direction.
Developing as a manager requires building pattern recognition about which tool is best for the job, which will largely depend on the context of the project, and the confidence and competence of your team.
An over-reliance on any one of these roles will make it hard for any manager to scale themselves and their teams.
Why Most Managers Aren’t Effective Coaches
Most managers are ineffective coaches because the art of coaching is undermodeled, underdeveloped, and undervalued, especially inside tech organizations where high volatility and ambiguity are the norms.
Let’s talk through each reason in more detail.
Coaching is undermodeled
You can’t be what you can’t see
Most managers have not been on the receiving end of great coaching themselves — at least within their organization — so they have few examples of behaviors they can emulate.
Annie Riley, who leads the manager training program at Fort Light, was exposed to the power of coaching for the first time as a VP at HotelTonight.
“Working with a coach changed my work life and personal life profoundly. Ever since I’ve been really motivated to bring the skills and tools that I learned from my own coach to others because there’s not a lot of good modeling around the situations in the workplace where you can and should be a great coach.”
Frequent behavior modeling can easily create fixed cultural norms about what management looks like and does at your company.
Once there’s a critical mass of managers who focus more on directing and evaluating vs. coaching, that becomes the primary unit of exchange between managers and reports, and teams can easily end up disempowered and mistrusting.
“Managing usually requires you to start by understanding the needs of the company and then trying to fit the goals of the individuals into those needs,” says Adam Grenier, who has built and managed teams at Lambda School and Uber.
Being a manager accountable to the company first means that coaching is substantially less prioritized and visible.
External coaches are not attached to the outcomes of your decisions. They are impartial third parties that can bear witness to your challenges to help you move through them.
Unfortunately, most teams aren’t going to be able to use an external coach to solve every problem they run into. So it’s on you to expand your coaching toolbox and help your team take on new challenges.
Switching modes feels uncomfortable
There is no simple playbook for management about when to use coaching, directing, or evaluating performance.
In reality, most work situations are interpersonal, nuanced, and require managers to toggle between these different modes nimbly.
Imagine a report comes to you seeking support around an interpersonal dilemma.
Asking “Have you tried these 3 things?” is a directing-oriented question, focused on giving advice based on context or expertise you may have.
Asking “What have you tried so far, and what did you learn in the process?” is a coaching-oriented question, focused on increasing openness and helping someone identify their next step.
It’s extremely rare to see managers model the switch between these modes effectively. It’s hard to build competence to tease apart which areas of a program require directing, and which pose an opportunity for coaching.
It requires clarity and confidence to know which one is most helpful for your report and why.
Managers will struggle to scale themselves if they aren’t spending enough time helping their reports to develop. In turn, their reports are likely to feel under-utilized and unmotivated.
Coaching is undervalued
The tech industry as a whole undervalues things that cannot be explicitly measured and are obsessed with constantly delivering value.
Managers are then incentivized to focus on work output rather than spending time thinking about the motivations and working styles of their employees that might lead to more effective output over the long run.
Short-term wins tend to be more important than long-term team development.
Ada Chen Rekhi has seen managers become too focused on the project management tasks in their roles without really thinking about the people getting the work done.
“Many people hold the misconception that coaching is just talking about your feelings and personal life at work. That’s wrong — coaching at the workplace is about more effective dialogue and aligning goals and motivations to get work done.”
Though its primary goal is to help unblock people and move towards more optionality and choice, coaching has the added value of surfacing high-fidelity information to managers so they can more effectively direct their teams.
A manager who knows what’s motivating an employee can use that information to consider future project assignments.
Ada shared that “Unearthing motivations or issues around execution through coaching can often point to things directly under the manager’s control. The primary thing may be a change in the manager’s behavior rather than the reports’.”
A manager who can use coaching to solicit, receive and action this kind of feedback can quickly establish rapport and respect.
Coaching is underdeveloped
Lack of training leads to over or under-coaching
Coaching is under-modeled and undervalued because it’s dramatically underdeveloped.
The tech industry is overly focused on training around strategic and functional domain expertise instead of interpersonal skills and intellectual humility.
Developing coaching skills — which are inherently relational and cannot be practiced alone — requires intentionally reconstituting these priorities.
Jean Hsu, VP of Engineering at Range, has coached engineering leaders for many years. In our conversation, she underscored that building coaching skills require going against the status quo of the training we receive and how we incentivize employees.
“Even for people who want to be supportive managers and not command-and-control-type managers, tech is an industry where people are used to solving problems, and that’s what they’re paid for. So it’s incredibly hard for people to withhold the “solving” parts of their brain, especially if you’re in a leadership position.”
Without solid training, managers fill in the gaps with misconceptions about what coaching is and when to use it.
Some managers will over-coach when a scenario calls for directing or evaluating. For example, they give constructive feedback about how a project was handled.
Ada Chen Rekhi says that coaching should never be a substitute for performance management though.
“If someone is not doing their job, coaching is part of your management toolkit to lead with inquiry and deliver feedback constructively. But at the end of the day, if someone is not getting the work done, you need to manage their performance.”
Most managers will under-coach, defaulting instead to directive behaviors about how to get the work done because the manager may have their relevant context and expertise.
Elena Luneva, General Manager at Braintrust, believes that a hands-off manager can be just as harmful to a team as a micromanager.
“They end up being the talking-head who is focused on vision and strategy but is completely absent from the growth of the team. This breeds mistrust drives top performers to leave, and causes managers’ to plateau in their growth.”
The most important thing is knowing which tool fits each job or task, which usually happens through explicit training.
Coaching skills require real training
Remember, coaching is about helping people see more options and make deliberate choices to unlock their answers instead of relying on yours.
Removing yourself from the center of the conversation can be scary to managers, who often feel like they’re supposed to help, know the answer, or be able to solve problems for their reports.
This is achieved through three primary skills, framed beautifully by Annie Riley:
Self-management: Knowing how to monitor and manage your internal world — your thoughts, beliefs, feelings, narratives, judgments, and insecurities — as you interact with someone else
Supportive listening: Hearing both what is and is not being said with a mindset of openness, calm, clarity, and care
Inquiry: Framing and asking the right questions — from a place of genuine care and curiosity — that enable someone to generate novel ideas and options
I know very few people who have meaningful training in these skills because most roles don’t explicitly require them.
However, your ability to hold space for others by being great at self-managing is the single biggest determining factor of your coaching efficacy.
Startups are stressful environments with turbulence and ambiguity. Some people thrive in these scenarios.
But I’d argue that most of us struggle more than we’d like to admit with self-doubt and lack of control in these environments.
It’s critical to be aware of how you’re feeling, whether you’re attached to certain outcomes, and which of your insecurities may be in the drivers’ seat.
These things can easily permeate a coaching conversation. If your report feels judged, dismissed, misunderstood, or ignored, the conditions aren’t right for a supportive conversation.
When she first started coaching, Annie found it incredibly difficult to self-manage in this way.
“I’d show up to coaching and my thoughts, feelings, reactions, and agendas would just be so loud. I know I’m not alone here. It’s particularly hard for People Managers to self-manage because they’ve often done the job themselves and it’s a big challenge to hold yourself back from just handing someone your playbook.”
Work like this takes real training and practice because we are all used to being the heroes of our own stories.
How to kickstart more coaching today
Individuals can’t single-handedly change that coaching is under-modeled and undervalued.
But each of us can learn coaching skills to become even more powerful people managers. The more of us that do it, the faster we can model it and show its value.
And any organization truly focused on a commitment to growth will incentivize managers to develop these skills.
Here are some strategies that I’ve used to help leaders integrate more coaching into their management practices.
Identify your competency focus
Determine your weakest coaching competency and start working to improve that skill. Soliciting feedback from your peers can be a helpful guidepost for where to start.
Self-management includes becoming aware of all the different feelings inside you, including where they come up in your body, and being able to name and actually feel emotional states that are granular and specific. It also includes being able to diffuse these feelings in real-time to stay present to the other person, rather than preparing your next question or trying to say the right next thing.
Supportive listening includes tuning into other people’s energy and body language, summarizing or reflecting for understanding, and holding space without judgment or labeling. People can feel when they’re in the presence of openness and trust, which are key ingredients to having a productive coaching conversation.
Inquiry includes digging into what’s going on underneath the surface and asking clear but open-ended questions to help people clarify and explore an idea further.
Once you’ve identified your focus areas, you’ll want to start enrolling others in your effort because coaching is inherently relational rather than something you do off in a corner alone.
Bring others into the process
Managers may be afraid to tell their teams that they’re working on a new coaching skill. But Annie says that everyone can benefit when managers are explicit about their intentions and bring their team into the process.
“I encourage something like this: It’s a new month, I’m trying to be a better coach, and I learned this thing and want to practice it. My intention for the next month is to be a great coach, so I’m going to be focusing on x. Here’s what role I’d love for you to play in it: please come to our next 1:1 with a challenge you’re facing and I’ll put on my coaching hat. And then after, you can tell me what worked for you, what was helpful, and even how I can improve.”
The tendency to want to learn new skills in secret is natural, but it’s unproductive for coaching. You can’t coach people in secret, and you’ll up-level way faster if you bring others along for the ride for feedback.
Plus, you’re now modeling what we so desperately need to see from managers!
Create the time and space by starting small
You don’t need to move mountains and carve out weeks or months to start practicing coaching skills. Keep it simple and small by using your existing 1:1s or business review meetings to wear your coaching hat.
Starting from scratch can be scary, so we asked our experts to share some tips on improving your self-management, supportive listening, and inquiry skills!
If you’re focused on self-management…
Ada Chen Rekhi - Find a way to run a 360 from your team. Take the 360 assessment yourself, and see whether there are any surprises or mismatches in how you intend to show up and how others perceive you.
Annie Riley - If you notice yourself feeling an urge to give advice or jump to solutions, then try breathing through it and naming what is going on. Labeling the specific emotion or impulse helps to diffuse it.
Adam Grenier - Do your best to forget everything about your own path to success, which is riddled with unique circumstances that are nearly impossible to replicate. Instead, focus on the other person’s needs and goals, then slowly introduce your lessons where they add value to the individual.
Elena Luneva - Your way is not the only way. When a solution that a team member comes up with is different from what you would choose, ask yourself: “Do they have the context you do?” If not, make sure they have the right context. Then, stay curious: their path may be equally or more effective, even if different.
Jean Hsu- Notice when you’re tempted to jump into problem-solving mode. Try to stay in a discovery or exploratory space for just a little bit longer.
Natalie Rothfels - After your 1:1 with a report, write down what emotions and physiological sensations you notice during your conversation.
If you’re focused on supportive listening…
Ada Chen Rekhi - Make it a practice to ask for specific feedback. Not “How am I doing?” but “What could I have done in that meeting?” And then listen with an intent to understand not to reply or defend.
Annie Riley - Validate and empathize without hijacking the conversation. It can help to picture an imaginary spotlight shining on the conversation. Try to keep the spotlight on the person that you’re coaching. If the spotlight starts to move away from them and onto you, then shift it back to focus on their thoughts and feelings.
Adam Grenier - Take an improv class or two. The “Yes, And” philosophy of improv has been so fundamental to my ability to listen and continue conversations to find what’s more important than anything else I’ve learned over the years.
Elena Luneva - Be present. Keep eye contact. Close the other windows with email or slack, pause your notifications and just imagine this is the only person in the world that matters right now. Naturally, your mind will wander through your mental task list. That’s ok, just bring it back to this person.
Jean Hsu - Get comfortable with more pauses in conversations, especially 1:1s. Often, when people are speaking, it’s after some silence that what’s important really comes through.
Natalie Rothfels - Notice and name the body language you sense when one of your reports is talking about what motivates or excites them. Asking a question about what they were excited about from the weekend is perfect…it doesn’t have to be strictly about work.
If you’re focused on inquiry…
Ada Chen Rekhi - Create space in your meetings where your team member owns the content. I will do this either by themed meetings with prompts such as “Career discussion - please come prepared with these questions” or agenda items, “Let’s debrief on this project and what went well and what didn’t.”
Annie Riley - Ask questions that start with “what” or “how” — these tend to be more open-ended questions and create space for more possibilities in the conversation
Adam Grenier - Ask for feedback. If you’re meeting with people regularly, ask them for frank feedback on why it works for them. Different people require different approaches, and until you understand why you’re good or bad at coaching different people, it will be hard to know which tools to use when and for whom.
Elena Luneva - Take off your expert, problem-solving, manager hat off and stay curious. Ask more questions than feels natural. Once the person is sharing answers, let them speak instead of attempting to show how brilliant you are.
Jean Hsu - Try asking “what else…” questions to give people space to go a little bit deeper. For example, “What else is going on? What else is important? What else?”
Natalie Rothfels - Ask something playful before diving into something serious. If each of you can access your own sense of childhood glee and spirit, you’ll have more access to creativity and optionality.
Supplement your 1:1s with a monthly coaching session, make clear goals and outline the intent of each session. Put it on the calendar so that it just happens, then solicit feedback from your report about what was most helpful.
Adam Grenier encourages folks to start with a mindset shift during this time: “Focus on needs in the moment and the goals of the individual over time.”
Rather than starting the conversation with “What are you doing?” or “What do you need me to do?”
This helps set the context that the space is for “introducing new ideas, paths, and opportunities that the individual can’t see or has never considered.”
If you can start adding just one of these practices into your 1:1s, you’ll be well on your way to becoming a great coach.
Wrap Up
Coaching is a simple, but not easy, tool that helps your reports get unstuck and enables you to scale.
“It’s a common misconception that, as a manager, you just hire someone senior from an A-list company, get out of their way, and you are done. There’s so much nuance that’s missing from that thinking: understanding team culture, collaboration, working styles, and the people already delivering at your company. Coaching can help with all of these, and up-level you and your entire team.” - Elena Luneva
Adding coaching to your toolkit alongside directing and evaluating will make your team significantly more impactful by helping each report reflect on and discover more about their own strengths, gaps, beliefs, and assumptions.
Even though it’s an underdeveloped skill, the good news is that you don’t need to completely shift how you’re managing today because coaching is additive.
Navigate your own internal landscape, take off your problem-solving hat so you can truly listen, and ask a few more supportive questions.
Before you know it, you’ll be on your way to more impactful management.