What You Can Do To Make Your Work With A Leadership Coach Or Mentor A Success
Summary:
To ensure a successful coaching or mentoring experience, establish clear goals and open communication with your coach or mentor. Understand the differences between coaching (focusing on growth through questions and challenges) and mentoring (sharing experiences and advice). Define what success looks like for you, and adapt with your coach to changes. Prepare for sessions, provide feedback, and stay committed to applying learnings. Regular check-ins and addressing any barriers can help you maximize what you get from working with a coach/mentor.
Many people go into coaching unsure of what to expect during the process, what they can ask of their coach, and what outcomes they can expect from coaching. It can feel even less clear if you’ve never worked with a coach before: You know you need someone to help you with something, whether it be a goal you’re working toward or a challenge you’re facing, but you may be unsure of how to actually get there with your coach.
In this post, you’ll find all you need to know about how to work with a coach/mentor so you can achieve your goals. You’ll learn
how to lay the foundations for a successful coaching/mentoring partnership,
how to get the most out of your coaching/mentoring sessions, and
how to identify and tackle barriers during the process.
I also go over a few examples of the different shapes of coaching so you have an idea of what you may ask your coach for and what you can expect. This guide is based on my own leadership coaching practice and feedback from my clients over the years, as well as my own experience partnering with coaches for five years while I worked as an engineering VP.
If you’re currently searching for a coach, I also recommend “How to Find an Effective Leadership Development Coach”, where you’ll find how to find the /right coach or mentor for you.
The difference between Coaching and mentoring
Coaching and mentoring are different tools that both serve your growth as a coachee/mentee and help you achieve your goals. While the tools differ, having open conversations about how you’ll work with your coach/mentor is crucial for success. In this article, I’ll refer primarily to coaching to make it easier to read, but all approaches are equally valuable for coaching and mentoring.
I offer both coaching and mentoring, but many coaches don’t. I always check in with my clients on how much they want of either. My only constraints are that I want to avoid giving unsolicited advice, and I also always want to make sure not to let the seeming ease of mentoring get in the way of the harder work on gnarlier topics through coaching.
Definitions
Coaching means using questions, challenges, and perspective shifts to help you grow and learn to think in different ways. It’s most helpful to learn new ways to think, solve problems, and make decisions, and be able to apply those by yourself in the long-term.
Mentoring means passing on ideas, thoughts, and experiences, either the mentor’s own or other leaders’, anonymized. It may also include sharing my opinions when asked, or collaborating as your sparring partner and giving feedback, e.g. on a new delivery process or re-org you’re designing. Mentoring is most useful when applied as a shortcut and to get to new ideas quickly.
What coaching vs. mentoring sound like
In coaching, your coach may say things like, “I’d like to challenge you a bit on what you just said”, “how do you think you want to solve this problem?”, or “let’s take a few steps back”.
In mentoring, your mentor may say things like, “I have a suggestion for you on this, would you like to hear it?”, “another client of mine had a similar issue, here’s what they found useful”.
How you’ll feel about your sessions based on coaching vs. mentoring
Coaching and mentoring are quite different, and what the person you work with offers will impact what your sessions together look and feel like, and what you take away from them.
Mentoring can often feel like you’re getting much more out of the time with your mentor at first: You get super concrete takeaways or hear specifics about what has worked for others and what hasn’t. If you have longer-term/bigger goals for how you want to grow as a leader, too much mentoring can also get in the way through too many “shortcuts” over the, admittedly more difficult, work of changing how you operate.
Coaching can sometimes feel a bit slower or even a little tedious or frustrating in comparison with mentoring because a big part of it is really exploring the complexity of a topic and your experience. This also means that it often comes with a lot of things to process, think about, and a lot of mental work. It also requires a lot of openness to being challenged on your ways of thinking or operating. It can be a tremendously useful tool, but these gains take more work and feel less like “easy wins.” You should still feel a sense of taking away positives from each session or making progress. But depending on your topics and goals, you may get important takeaways in every session, but it may take a little while until you get bigger breakthroughs.
How i work with coachees & mentees
Coaching is a substantial investment of time, money, and energy, not just for the sessions themselves, but also for putting takeaways into practice. To me as a coach, it’s important that my clients get as much as possible out of our work together, so their investment pays off for them.
When you sign up for coaching with me, my mission is to help you reach your full potential and accomplish your goals. I will become your number-one supporter: I will share tools, resources, and my experiences, provide encouragement and guidance to explore the “unknown unknowns”, and challenge you to go further than you think you can go—and let you know if I think you’re holding yourself back.
In return, I ask my clients to commit to doing the work in service of their growth, and to making the changes they need in order to operate from a place of clarity, decisiveness, creativity, and strength.
Coaching is an equal partnership. As a coach, I’m deeply committed and accountable to do all I can to help you succeed. Here’s what you can do from your side to maximize what you get out of a coaching engagement:
What coaching/mentoring engagements may look like
Like many other coaches, I offer different engagement models (contact me to learn more!), most commonly I work with clients for 6-8 months with sessions every two weeks. Here are the most common and, in my experience, most effective ones.
Engagement duration:
I offer to partner for a pre-defined number of sessions, with packages currently ranging from 10-20 sessions. For people who only want to try out coaching first, I also offer to meet a few times with a flexible model.
Frequency:
Most common, most effective: Meet every two weeks. Typically, this means we meet often enough to build solid momentum on various topics and maintain a high level of context on your situation. At the same time, you also have enough time in between to put takeaways and action items into practice, run experiments, and grow.
Weekly: Meeting weekly, or even multiple times a week, is best for people who deal with lots of changes or challenges at once and seek a lot of mentorship, including e.g. a sparring partner who they collaborate with on concrete topics. We typically transition to meeting fortnightly after some time.
Monthly and on-demand: Monthly or less frequent sessions work best if you either want more mentoring-based sessions or have a set of very long-term goals that you would like support in. This kind of setup requires a high degree of accountability and follow-through, but can also be quite valuable.
Session length: My coaching sessions are always 50 minutes long.
Foundations: a successful start to your coaching
Defining What success means for you
People have very different ideas of how coaching works. Many of my clients at first aren’t sure about how it works at all. And that’s okay! Coaching can take different shapes for different people. Similarly, success will look different for each person, too. It helps to have a first sense of that when you look for a coach, so both of you can assess if you’re a good fit for working together.
The most important thing you can do to get the most out of your work with a coach is understanding what success means for you, what has worked for you in previous coaching engagements or other training/learning experiences, and what hasn’t. Here are examples of the value some of my former clients got from our work together:
Case study: A newly-promoted Principal engineer feels more confident
“I chose to work with Lena when I was promoted into a principal role and I felt I needed to be prepared for the transition from individual contributor to a leadership position. I did not know what to expect from my new role. I did not quite know what skills I needed to brush up on either.
From the initial questionnaires through to the careful questions in the sessions, Lena helped me figure out what I needed to explore and unpack. Lena's great skill is that she listens and empathetically points out blind spots and suggests how to adjust perspective. This was invaluable as it meant I felt comfortable enough to be able to explore my vulnerabilities and figure out strategies to deal with them.
As a bonus she provided great resources that were relevant to our discussions in a follow up email after each session. After the series of sessions with Lena I feel more capable and confident to trust my decisions and leadership skills and have ways to experiment and improve and spot when things are not working.” — Maia G, Principal Engineer
Case study: An Engineering Director is prepared for a bigger role
“Lena helped me fill the skill gap I recognized while moving into a senior leadership position. Our sessions have been mainly focused on the unknown unknowns of my new role and on building a roadmap to follow to hit the ground running.” - Emanuele Giarlini, Director of Engineering
Case study: Challenges & New tools for a Head of Product Ops
“Lena was incredibly supportive, objective and practical with her advice. She challenged me about some of my ingrained habits and beliefs in a direct but thoughtful and kind manner. She provided me with practical tools that I could use immediately in my work. My team have seen a difference and are more engaged as a result.” — Selina, Head of Product Operations
My recommendation:
Define what success in coaching/mentoring will mean for you, e.g.: What do you want to learn? What challenges do you want to address? What goals would you like to achieve or make progress towards? How will you know that the investment in the coaching was worth it for you?
Setting goals together
You and your coach need to be on the same page in terms of what you are looking for, what “good” looks like for you, and how you learn.
In my coaching practice, I offer an intake questionnaire to help my clients and me design our partnership. This questionnaire goes over topics like values, strengths, areas of growth, career goals, how you spend your time at work, your support system, and includes a tool that helps you identify and quantify your leadership skills. It’s quite extensive, and with an important reason: A variety of variables that can impact what success looks like for the leaders, and a comprehensive view is important to do justice to the complex challenges many leaders deal with. The questionnaire is entirely optional, but everyone who’s taken it has reported that it’s helped them
Make space to think about topics they don’t often have or make room for in their busy lives
Recognize patterns and themes in their own behaviors that they weren’t as aware of
Take a different point of view on some of the challenges they’re facing
My clients and I walk through their responses together and design a coaching roadmap as a team. Through this approach, we speed up the context gathering, which means we can get to bigger topics faster. We also set tangible goals and, ultimately, what success means for our work together.
Creating a coaching roadmap (or not!)
Based on these goals, my clients and I create a roadmap. People are different, and I’m always open to adjusting based on their needs, so this roadmap can be as detailed or high-level as you like:
Super detailed goals & roadmap steps: I have a client who I work with on an ongoing monthly basis. They have very detailed personal and professional goals that they set for themselves. We review these goals every quarter and define our coaching focus areas based on those.
Most common: Concrete high-level goals, prioritized: This setup is similar to how many teams use roadmaps, with larger topics that get broken down into smaller tasks over time. As we prioritize and start tackling those, we dive deeper into what’s been challenging and what the leaders I work with have already tried to tackle them. This setup is quite useful because many leaders work in fast-changing organizations and this way we stay flexible in what we prioritize, while still making sure we’re on the same page. Such goals my clients set have included:
“Become more confident as a leader”
“Deal with adversity after returning from parental leave”
“Improve trust with stakeholders and engineering productivity”
“Improve performance of the engineering organization”
“Find a new leadership role where I can have the impact I want to bring”
Only directional goals, plus vibes regular check-ins: I have several clients with whom I work on an ongoing basis. We have only very high-level goals for our work together. In such a setup, I check in regularly to get feedback and adjust my approaches as-needed. These directional goals have included:
“Adjusting my role as a leader in a fast-changing, fast-growing organization”
“Upleveling performance of my organization”
“Having a support partner to talk ideas through with and challenge me”
Case Study: Ad-hoc goals & Ongoing coaching as space to reflect and be challenged
A C-level leader and I are typically only in touch during the coaching sessions. We meet every other week. A few minutes before, sometimes even into the session, they come up with their topic.
The most impactful part of the session for this client is talking over the issue. They get a ton of value from verbalizing their thoughts. They also find value in me challenging them regarding what they say, and occasionally hearing my opinion.
Because I have so much context about their organization and their team, I have also run offsite workshops for them. While I am primarily a coach for this C-level leader, I am also a partner that they can bring in for more considerable organizational challenges and training.
My recommendation:
Check in with yourself on how you like to set goals, and share it with your (prospective) coach.
Throughout the coaching partnership
Giving feedback & Checking in on progress
Communication with your coach about the coaching is also important. Having a meta-conversation about the coaching is necessary, not just at the beginning of your partnership but also as things move along.
I let my clients know that their thoughts and opinions are welcome, and regularly ask them for feedback; with leaders who I have a limited engagement with, e.g. for 6-8 months, I also do a more structured check-in halfway through. I want to know if they feel like things are going well generally, if something we’re doing is particularly helpful, or if there is something we need to change.
Case Study: Shifting from mentoring to more coaching over time based on changed needs
A senior engineering manager I worked with initially wanted mostly mentoring from our work together. They had just transferred to a new team in their scaleup and had many difficult, new-to-them situations to navigate: A new boss, a newly-formed team, and extra pressure through important company goals their team was working on.
In our initial conversations, they already mentioned that they’d like to transition out of mentoring over time. As time went on, I checked in with them every few sessions about how our sessions were working for them. Over time, as they got more into their new role, we shifted from more tactical and reactive topics to more strategic and long-term ones, like growing their career longer-term and towards a promotion, and getting more visibility from senior leaders.
Before your session: Preparing (or not)
Some of my clients like to prepare for our sessions and share context with me already so we can jump right into the topics once we begin. Others don’t, and that also works! Here are some examples so you can
Case study: sharing context in writing before sessions
A VP-level executive I work with shares a written update with me before each of our sessions. They cover what has happened since our last session, their progress on action items, and their topics for our next session.
They get value from reflecting on the past month and writing it down. By sending me their reflections ahead of time, we get the benefit of getting the context laid out before our session, so we can jump into things when we meet up. We also occasionally work async together on documents, like when they’re prepping talking points for a particularly stressful team meeting.
What you can ask for during coaching
Each person has different needs and different methods of working together help them succeed. My goal as a coach/mentor is to offer what’s most useful to them, which can also change over time. I want to share some of the ways I work with clients that they have found helpful, so you get a sense of what you may be able to ask for:
Third-party perspectives: It can be helpful to have someone to talk to who is not entangled in the power dynamics of your company and is not the person in charge of whether you get a promotion. Clients often ask for a reality check/”sanity check”: “Is it just me who’s dealing with this challenge?”, “Do things like what I experience happen in other companies too?” — I meet with dozens of companies every month, so I have a lot of insight into how different organizations work. Granted, my answer is often “no, you’re not the only one dealing with issues like this”, or “no, what you’re dealing with isn’t ‘normal.’"
Validation of issues that are happening: On a similar vein, many coachees get value out of knowing they are not the only person dealing with a specific problem.
Practicing new ways of communicating and working: I regularly use our coaching sessions to help my clients practice new ways of communicating, whether it’s an important update you’re giving to your boss or a difficult decision you have to deliver to your direct reports, or you want to change the way you speak, e.g. to sound more confident. As the coaching relationship is a trusting space, it can be a good place to experiment and get feedback quickly.
Case studies: Using coaching sessions to practice new skills
A client wasn’t confident in their communication in English as it isn’t their native language and they were concerned that their upbringing in a culture where communication is more indirect was negatively impacting their work in a workplace that emphasized direct communication. We used our coaching time to practice what they wanted to say and help them develop new communication tools, as well as ways to help their multicultural team embrace different ways of communicating.
A client wanted to get better at communicating with executives. We used the preparation of our sessions as well as how we talked with each other to practice communicating more concisely, summarizing, and bringing more clarity.
Modeling good leadership behaviors: In my coaching sessions, I always try to model the behaviors that make a good leader to help demonstrate what that looks like. Some people have had poor experiences with leaders in their organization and need a good example they can observe. A recent occurrence of this happening was when my client shared that she was in a high-stakes meeting with other executives. After something she needed to respond to was said, she found herself wondering, ‘What would Lena say in a situation like this?’, and it helped her formulate a response.
Sharing resources: I always happily share resources like articles, videos, or guides with my clients and they know they can ask for those, or I’ll offer if I have something in mind.
Staying in touch between sessions & getting accountability support: Some clients find value in touching base between our coaching sessions. Sometimes they want to give me updates and others check-in for accountability purposes, or I check in with them to ask about their progress. There is a limit to how quickly and how often coaches can respond to emails, so it’s beneficial to discuss communication preferences and needs with your coach.
A reality check: Clients tend to find useful an extra perspective and reality check useful. Sometimes, they will come to me with questions like, “Am i doing things wrong or is there something going wrong in my environment?”
I hope this demonstrates that coaching is not a one-size-fits-all ordeal. There are quite of few different ways to get value out of coaching and you can choose those that works best for you. A good coach will still offer variability to how they deliver the coaching.
My recommendation:
Ask your (prospective) coach about what tools they like to use, and which ones they find useful. Give them feedback about what’s worked well for you and what hasn’t so they can adjust.
Barriers that may get in the way and how to handle them
Sometimes challenges pop up that keep clients from getting the most out of their coaching. As a coach, whenever I (think that I) notice such challenges, I always raise it as an observational question and an invitation to chat about what may be causing or contributing to those issues.
I never judge, but I always inquire. Ultimately, coaching dynamics tend to reflect issues that we face in other areas of our lives as well, or over time symptoms show up that are similar to what you deal with in your work too. Therefore, reflecting on those issues together has often led to bigger breakthroughs for my clients in understanding what’s getting in the way of their growth.
Case study: Using challenges in the coaching work to address bigger issues
A client really struggled with making space for the action items that they committed to in our sessions. We talked about what made it so difficult and realized that they’d gotten stuck in a very reactive, almost frantic work mode and felt like they were just fighting fires all the time. As a result, we came up with several steps for them to change how their calendar is organized, how they communicate updates and priorities with their stakeholders, making space for more strategic work, and changing how they triage and prioritize their own work. We also stayed in touch more in between our sessions, as they found it helpful to get regular check-ins from me with reminders.
Very soon, they were able to much more diligently implement the action items from our sessions. At least equally importantly though, the way their role and work felt for them started changing: Out of the reactive fire-fighting, towards a calmer way of leading and feeling more in control.
All of the examples of barriers can happen occasionally - we’re all human, after all. But I found that when they become more common or there are patterns, it’s usually a symptom of a bigger underlying problem.
Examples of these barriers & how to handle them:
Meeting frequency: An appropriate frequency of meetings is necessary for staying up to date on progress and for accountability purposes. The actual frequency, i.e. weekly, bi-weekly, monthly, etc., will depend on your goals. What’s important is being consistent and adjusting as needed, staying connected, and keeping on-topic based on the roadmap created with your coach.
Regularly canceling sessions on short notice: Each coach has a different policy on this. I share mine with clients as we begin our work together, this is it: The majority of my work is pre-arranged with busy clients like you. It's typically not possible to fill a slot on short notice, which means that short-notice cancellations result in a meeting spot going unused. Therefore, I ask for at least 24 hours’ notice if clients need to cancel or move a meeting. I always do my best to be flexible and accommodate in emergency situations, but with shorter-notice cancellations, I reserve the right to consider the session as delivered.
Lack of action and accountability: Nothing gets solved in coaching: Talking through your goal will only take you so far. When you have a goal, you will need to own that goal and take steps toward meeting it. Similarly, if a goal doesn’t pan out the way you’d hoped, do your best to own it so you can move forward. This includes talking about it with your coach: If you didn’t get to prioritizing action items, what got in the way? What does that tell you about how you work? What do you want to change based on this experience?
Coaching methods aren’t working: Your coach should always be open to receiving feedback, so they can offer different approaches or tools as-needed. If something seems like it would help initially, but it ultimately does not, you can voice this to your coach.
Coaching vs. mentoring mix isn’t useful: You may need more direct support occasionally, e.g. to get unstuck. You can always mention this if your coach does both.
Changes: To ensure everyone is on the same page, it always helps to share when things change, like goals, needs, your company’s strategy, etc. Your coach can deal with changes, but they need to know what’s going on to do so.
Using coaching sessions purely as venting sessions: Venting can be helpful and is often helpful for getting context about a situation. However, a coach is usually most useful to help you figure out how to move forward. Sometimes, you may at first need to vent, and that’s okay too! But getting stuck on it or spending too much time venting can derail achieving your goals.
Fear around difficult topics: Clients sometimes get concerned or apologetic when bringing up difficult topics. I work with many highly empathetic, caring leaders, and while it’s a kind sentiment to consider how topics may impact me, it’s also important to me that the folks I work with know that they can bring those things to me. In my coaching practice, I’ve worked with a lot of folks who are facing discrimination or harassment, working with very difficult bosses, in toxic companies, and many other awful challenges. Please know that it’s okay to bring up those types of topics. If a difficult topic is impacting you at work and you want to bring it into the coaching, then bring it up. Your coach can handle tough conversations! If a topic or problem is out of the scope of what your coach can help you with, or e.g. veers more into therapy territory, they will let you know, and they may still be able to help you figure out what to do next to work toward addressing that topic.
Staying aligned with your organization: When outside individuals are invested in your coaching, like your boss or a people leader, it’s important to stay in touch with them regarding coaching topics: Let them know what you’re working on with your coach, or share the roadmap with them. By doing so, you’re also gaining experience in managing up.
My recommendation: Give your coach feedback!
Occasionally, a coachee may become frustrated with the coaching process if they feel they are not making progress toward their goals. This is a completely understandable feeling, and super important to notice!
Share this with your coach so you can work together to identify where the problem lies and if/how you’re able to address it together. Above all, you and your coach are a team, and your coach wants to do their best to help you succeed in your goals.
Sometimes, the process of doing this involves adjustments or identifying where you’re getting stuck or what’s not working well about your partnership. It may also mean realizing that you and your coach are not a good fit for working together after all. That’s okay!
Whether you’re actively being coached or are searching for a coach, know that you can use tools to make the most of your work with your coach. You don’t have to be afraid to ask for what you need. There are so many ways to be coached and to get value out of coaching, and so many different ways to make your work with your coach a success. Knowing what is even possible to ask for and what you can expect to happen while being coached will help you start your coaching journey with confidence.
