How to find an effective leadership development coach
So, you’ve decided to take the leap and explore leadership development coaching. That’s great! It can be a hugely rewarding experience that allows you to unlock your potential and learn how to be a better leader.
Coaching has become increasingly popular amongst leaders at all levels in the tech space, from engineering managers, to directors, and executives like CTOs and VPs, which means there are more options to choose from. As a result, finding an effective leadership coach can feel like a daunting task. It’s important to find someone who can be a trusted partner - you’ll form a relationship with this person, so it should be someone who can offer you a safe space to share and discuss challenges, and provide valuable insights, strategies, and tools to help you overcome these challenges, develop your leadership potential, and achieve success in the areas that matter to you.
Reasons to work with a coach
I worked with leadership and executive coaches myself for five years in my time as VP Engineering with Travis CI and CircleCI. Initially, I asked my boss at the time to support executive coaching for me as the company was going through lots of turmoil. Over time, having a sparring partner proved to be invaluable. Here are some key areas where coaching could help you:
Preparedness: Getting ready for a career transition or moving to a higher-level role.
Newness: Moving into a new role, starting to manage a new team, or changing companies or industries.
Dealing with change: Leading cultural transformations, finding your place again after a merger or acquisition, or when you get a new boss or team or your company is going through downsizing.
Feeling stuck, getting unstuck: Coaching can help you get to a place where you feel less stuck in your role or career and feel like you have more options available to you.
What questions should you ask on your quest to find the right coach? I’ve put together a list of the key things to consider as you start your search.
Should I work with a coach or a mentor?
Depending on your needs, find someone who offers mentoring and coaching, or “pure” coaching. Both have their place and can be very useful. The definitions that I find most useful are:
Mentoring means passing on ideas, thoughts, and experiences, either their own or (anonymized!) experiences that other clients had, as well as collaborating on ideas and giving feedback, e.g., a new delivery process you’re designing. 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”. Mentoring can be a shortcut, and useful to get to new ideas quickly. It means that your coach utilizes their own, and others’, experiences to help you grow.
Coaching means using questions, challenges, and perspective shifts to help you grow and learn to think in different ways. It means equipping you with practical new thinking tools and approaches. In coaching, a 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 and think about this at a higher level”. It means using questions and challenges as tools for reflection and growth.
What should I look for in a coach?
Here are five things you should look for in a coach:
You click with them. Don’t make coaching harder than it needs to be. Find someone who you have good chemistry with and who you can trust to talk about hard stuff early on; the more open that you feel you can be with them, the faster you’ll be able to progress in your work together. Many coaches offer a free introductory session for getting to know each other - use this as a way to check if you have rapport. Trust your intuition.
Their process and approach jive with how you like to work. If you’re a very ad-hoc, spontaneous person who’s looking for a sparring partner to discuss ideas with, someone with a very strict coaching-oriented mindset may not be a good fit for you.
You share similar values. Read/watch the coach’s work online, e.g., in articles or talks that they published, to see if their way of thinking resonates with you.
They offer the kind of support that you’re looking for. Coaching engagements can vary - some coaches offer more short-term collaborations (1-4 sessions), others only offer longer-term partnerships (3-6 months or longer). Typically:
Short-term engagements are helpful for addressing a very concrete challenge or problem.
Longer-term coaching is helpful for addressing tactical topics, but also pursuing longer-term challenges and goals. This is a good fit for topics like: Growing into or getting ready for a new role, developing a better relationship with bosses and stakeholders, becoming more confident or addressing imposter syndrome, increasing your impact as a manager, or dealing with challenging situations at work.
How you like to stay in touch. Some coaches offer support in between sessions, e.g., via email or text, others don’t. Consider your preferred communication style and frequency, and try to match this in your coach.
How do I measure if my coach is effective?
What makes an effective coach depends on each individual, but common measures are:
They listen effectively. Meaning, they make sure they correctly hear what you’re trying to say, and actually understand and empathize.
You feel seen and get what you need. Many coaching clients come to me for help in getting unstuck or dealing with big challenges. When a client comes into a session tired, and leaves feeling good about new options and excited to try out some experiments they came up with, that’s a sign of effective coaching.
Achieving your goals. If your coaching helps you achieve your goals, that’s huge. It can be worth setting goals and expectations at the start of a new coaching partnership to help set a clear direction.
Should my coach have similar experiences to the experience I want to build?
It depends on what you’re looking for. It’s more important if you’re looking for a mentor. It can, for example, be helpful for an engineering leader to identify the “unknown unknowns” of their role when working with someone who’s been in a similar role. Even then, the coach needs to make sure that they’re not projecting their own experiences, but working with the coaching clients to bring light to these uncertainties. That said, you may benefit tremendously from working with someone outside your field. Ultimately, what matters most is that you’re comfortable with them challenging you!
What my coaching approach and process looks like
Now that I’ve covered coaching in general, drawing on my own experiences as a coachee, I’ll give you an overview of my own practice as a leadership coach. Hopefully this will give you some inspiration for what to look for or figure out what’s important to you, as you embark on your own journey to finding the right coach for you and your needs.
I start with a free introduction to check chemistry and expectations. We use this time to talk about what the potential client wants to get out of coaching, as well as any questions you may have. I share my process and we discuss logistics (how long do you envision us working together? How often would you like to meet?). Ultimately, the goal of this session is to help us both get a sense if we’re a good fit for working together.
My coaching process is fairly structured with most of my clients and includes longer-term goals, but with a few clients, it’s a bit looser.
I offer mostly coaching, with some mentoring sprinkled in. With some clients, it’s 99% coaching, with others a 60/40 mix of coaching and mentoring. The mix depends on my client and their needs, which is the most important aspect to me. My only rule is that I never want to offer unsolicited advice, so this is a topic I discuss with potential clients and alter based on their wishes. Usually, my mentoring is focused on organizational challenges only; when it comes to personal development, which is so highly impacted by who we are as individuals, coaching is much more powerful.
My main goal as a coach is to help my clients accelerate their growth by learning faster in a space where it’s safe to fail.
The main pillars of my coaching practice are accountability and playfulness:
Accountability means that my role is holding you to your growth goals. In practice, it means:
We start off with an in-depth context gathering questionnaire that covers questions like your values, support system, organizational context, career goals, as well as how you learn best. This questionnaire serves a few purposes:
It helps me get a better picture of who you are, what matters to you, and how to best support you.
It connects you again with what matters most to you, therefore creating the foundation for our work together.
Together, we spend one coaching session walking through your responses; to this session, I bring first ideas of themes and potential coaching topics, which we discuss and turn into,
A coaching roadmap and goals, which we prioritize. These goals serve as an agreement about what we want to focus on, and help us stay on track. In addition, there’s,
Accountability between sessions. My coaching work typically includes follow-up work (I don’t say “homework” as it’s not added work, but embedded in the work you do anyway). And that’s where the second pillar comes in.
Playfulness. Most of my clients are very experienced, with 10+ years of experience in the workplace. This also means that their challenges are often big, gnarly questions that they weren’t able to figure out themselves, even after trying out some ideas - questions like: “I feel stuck in my role”, “I want to grow to a higher-level role, but don’t have internal support”, or “my boss sucks”. So we usually:
Break down the problem into smaller chunks
Develop hypotheses
Try things out. This means that in our sessions, we develop ideas and options for you to test, like: New communication tools to get aligned with your boss, experiments to run to get better feedback, or ways to identify higher-impact work. You try these out in between our sessions, and return with lessons learned. Not everything will work out at first try, but it’s all useful information which we build on from there.
“Nothing gets solved in coaching sessions - we develop ideas and options for you to try out, and the real work happens in between. Leadership is in our actions, and building out our tools and confidence is in taking steps and learning quickly.”
There’s a lot to think about with coaching, but by taking the time to find the right leadership coach, you can maximize the benefits and achieve greater success in your work as a leader and manager. Remember, trust will always be the most important component of a coaching relationship, so use your first meet to test for chemistry. Make sure you feel this coach will have your back, but challenge you when needed (from a place of support and understanding!).
If you’d like to find out more about coaching with me and take me up on a free introductory chat, please get in touch. You can see some of the things my coaching clients have said about our work together below.
“Finely balancing coaching, mentoring and emotional support, Lena is a key contributor to my leadership growth and professional development. While I often times have a rough idea of how to navigate complex situations, Lena helps me crystallize my instincts, fortify my approach by challenging me with her seasoned executive mindset and turn bits and pieces into an actionable plan. Lena empowers you through coaching, and keeps you accountable to your own success.”
— Senior Engineering Manager
“I started working with Lena when I began my first role as an engineering manager and she was a tremendous support as I faced the challenges and unknowns that came with that big change. She was able to guide me through distracting details to uncover the goals, questions, and outcomes that I actually needed to focus on. The resources Lena provided me with helped me to show up for my team as the manager they deserved.”
— Engineering Manager
“When I started working with Lena I wanted to focus on creating a dedicated people management role in my engineering organization and begin scaling the efficiency of our growing organization. Lena played a strong role in helping me execute these goals. Her ability to listen, provide insight, and challenge me to think differently made me more aware of what I was capable of as a manager. From the outset, the process and guidance provided were beneficial.”
— Head of Engineering
