Mentorship, Coaching, and Building Resilient Teams | Pluralsight

Taking on an engineering leadership role can be disorienting for fresh recruits from the engineering ranks and seasoned veterans alike. The job throws rocks in the road at nearly every turn—and Lara Hogan has encountered just about all of them.

Hogan spent more than a decade leveling up engineering organizations and growing leaders at companies like Etsy (as an Engineering Director) and Kickstarter (as VP of Engineering). She took her experience and co-founded Wherewithall, where she offers one-on-one coaching services for managers, executives, and individual contributors growing into leadership, and consulting services to support engineering organizations.

Through those experiences, she learned to gracefully hire engineers, conduct difficult conversations, and mentor and coach other leaders to do the same. She wasn’t born a manager, though—like many engineering leaders, she started out doing multiple front-end development jobs.

“Along the way, I realized I wanted to be a manager, and my story's been written ever since,” Hogan says. “I loved it. I'm one of those weirdos who knew I wanted to manage, and it was the most fulfilling thing for me.”

Yet she’s worked with a lot of engineering leaders where that internal drive—and the resulting fulfillment—weren’t the case. They run into the same struggles and the same problems she did, but there was no handy guidebook for them to consult along the way.

So she wrote one. It’s called Resilient Management, and it’s being released into the world today.

“It’s incredible to me how common these core challenges are for managers (and the management-curious!) in the tech industry,” Hogan says. “It’s been an honor to try and craft a resource to support managers as they weather this kind of work. I want to try and reach as many of these folks as I can—I deeply believe this book is going to help them immensely.”

Resilient Management is Hogan’s third book, and the first to focus entirely on the ever-shifting world of engineering management and people-leadership. “As engineers, we have that solid internal barometer of success,” she says. “We know what it looks like to succeed. We know what it looks like to be productive. But managers have to start over—you don't have an internal barometer anymore. Management is about developing that new internal spidey sense. Maybe your people need strategy. Maybe your people need some hand-holding, or maybe your people need you to get out of the way. It could be so many different things. Figuring out what you should be counting your progress by, it’s unique to your situation, your company's situation, what your direct reports need.”

One of the ideas in Hogan’s book that struck a deep chord with us is how an engineering leader can take on the different roles of mentor, coach, and sponsor. Many managers—even those with training—often slip most comfortably into the mentorship role, because it’s so solutions-driven. Coaching and sponsorship, however, can lead to much more meaningful and longer-lasting growth, and they are much more frequently misunderstood even by long-time leaders.

In this excerpt from Resilient Management, Hogan explains each of these roles. She delves into the communication strategies that managers can use to better coach their teammates, as well as the contexts in which managers can become more effective sponsors for their reports within the wider organization—particularly for members of underrepresented groups.

Below is an excerpt from Lara Hogan’s new book, Resilient Management, now available in paperback and digital formats.

Mentoring

When I talk to managers, I find that the vast majority have their mentor hats on ninety percent of the time when they’re working with their teammates. It’s natural!

In mentoring mode, we’re doling out advice, sharing our perspective, and helping someone else problem solve based on that information. Our personal experiences are often what we can talk most confidently about! For this reason, mentorship mode can feel really good and effective for the mentor. Having that mentor hat on can help the other person overcome a roadblock or know which next steps to take, while avoiding drastic errors that they wouldn’t have seen coming otherwise.

As a mentor, it’s your responsibility to give advice that’s current and sensitive to the changing dialog happening in our industry. Advice that might work for one person (“Be louder in meetings!” or “Ask your boss for a raise!”) may undermine someone else, because members of underrepresented groups are unconsciously assessed and treated differently. For example, research has shown that “when women are collaborative and communal, they are not perceived as competent—but when they emphasize their competence, they’re seen as cold and unlikable, in a classic ‘double bind’.”

If you are not a member of a marginalized group, and you have a mentee who is, please be a responsible mentor! Try to be aware of the way members of underrepresented groups are perceived, and the unconscious bias that might be at play in your mentee’s work environment. When you have your mentor hat on, do lots of gut checking to make sure that your advice is going to be helpful in practice for your mentee.

Mentoring is ideal when the mentee is new to their role or to the organization; they need to learn the ropes from someone who has firsthand experience. It’s also ideal when your teammate is working on a problem and has tried out a few different approaches, but still feels stumped; this is why practices like pair coding can help folks learn new things.

As mentors, we want our mentees to reach beyond us, because our mentees’ success is ultimately our success. Mentorship relationships evolve over time, because each party is growing. Imaginative, innovative ideas often come from people who have never seen a particular challenge before, so if your mentee comes up with a creative solution on their own that you wouldn’t have thought of, be excited for them—don’t just focus on the ways that you’ve done it or seen it done before.

Managers often default to mentoring mode because it feels like the fastest way to solve a problem, but it falls short in helping your teammate connect their own dots. For that, we’ll look to coaching.

Coaching

In mentoring mode, you’re focused on both the problem and the solution. You’ll share what you as the mentor would do or have done in this situation. This means you’re more focused on yourself, and less on the person who is sitting in front of you.

In coaching mode—an extremely powerful but often underutilized mode—you’re doing two primary things:

1. Asking open questions to help the other person explore more of the shape of the topic, rather than staying at the surface level.
2. Reflecting, which is like holding up a mirror for the other person and describing what you see or hear, or asking them to reflect for themselves.

These two tools will help you become your teammate’s fiercest champion.

OPEN QUESTIONS

“Closed” questions can only be answered with yes or no. Open questions often start with who, what, when, where, why, and how. But the best open questions are about the problem, not the solution. Questions that start with why tend to make the other person feel judged, and questions that start with how tend to go into problem solving mode—both of which we want to avoid while in coaching mode.

However, what questions can be authentically curious! When someone comes to you with a challenge, try asking questions like:

• What’s most important to you about it?
• What’s holding you back?
• What does success look like?

Let’s say my teammate comes to me and says they’re ready for a promotion. Open questions could help this teammate explore what this promotion means and demonstrate to me what introspection they’ve already done around it. Rather than telling them what I think is necessary for them to be promoted, I could instead open up this conversation by asking them:

• What would you be able to do in the new level that you can’t do in your current one?
• What skills are required in the new level? What are some ways that you’ve honed those skills?
• Who are the people already at that level that you want to emulate? What about them do you want to emulate?

Their answers would give me a place to start coaching. These questions might push my teammate to think more deeply about what this promotion means, rather than allowing them to stay surface level and believe that a promotion is about checking off a lot of boxes on a list. Their answers might also open my eyes to things that I hadn’t seen before, like a piece of work that my teammate had accomplished that made a huge impact. But most important, going into coaching mode would start a two-way conversation with this teammate, which would help make an otherwise tricky conversation feel more like a shared exploration.

Open questions, asked from a place of genuine curiosity, help people feel seen and heard. However, if the way you ask your questions comes across as judgy or like you’ve already made some assumptions, then your questions aren’t truly open (and your teammate can smell this on you!). Practice your intonation to make sure your open questions are actually curious and open.

By the way, forming lots of open questions (instead of problem solving questions, or giving advice) is tremendously hard for most people. Don’t worry if you don’t get the hang of it at first; it takes a lot of practice and intention over time to default to coaching mode rather than mentoring mode. I promise, it’s worth it.

REFLECTIONS

Just like open questions, reflections help the other person feel seen and heard, and to explore the topic more deeply.

It’s almost comical how rarely we get the sense that the person we’re talking to is actively listening to us, or focusing entirely on helping us connect our own dots. Help your teammates reflect by repeating back to them what you hear them say, as in:

• “What I’m hearing you say is that you’re frustrated with how this project is going. Is that right?”
• “What I know to be true about you is how deeply you care about your teammates’ feelings.”

In each of these examples, you are holding up a metaphorical mirror to your teammate, and helping them look into it. You can coach them to reflect, too:

• “How does this new architecture project map to your goals?”
• “Let’s reflect on where you were this time last year and how far you’ve come.”

Occasionally, you might get a reflection wrong; this gives the other person an opportunity to realize something new about their topic, like the words they’re choosing aren’t quite right, or there’s another underlying issue that should be explored. So don’t be worried about giving a bad reflection; reflecting back what you’re hearing will still help your teammate.

The act of reflecting can help the other person do a gut check to make sure they’re approaching their topic holistically. Sometimes the act of reflection forces (encourages?) the other person to do some really hard work: introspection. Introspection creates an opportunity for them to realize new aspects of the problem, options they can choose from, or deeper meanings that hadn’t occurred to them before—which often ends up being a nice shortcut to the right solution. Or, even better, the right problem statement.

When you have your coaching hat on, you don’t need to have all the answers, or even fully understand the problem that your teammate is wrestling with; you’re just there as a mirror and as a question-asker, to help prompt the other person to think deeply and come to some new, interesting conclusions. Frankly, it may not feel all that effective when you’re in coaching mode, but I promise, coaching can generate way more growth for that other person than just giving them advice or sharing your perspective.

Choose coaching when you’re looking to help someone (especially an emerging leader) hone their strategic thinking skills, grow their leadership aptitude, and craft their own path forward. Coaching mode is all about helping your teammate develop their own brain wrinkles, rather than telling them how you would do something. The introspection and creativity it inspires create deeper and longer-lasting growth.

Sponsoring

While you wear the mentoring and coaching hats around your teammates, the sponsor hat is more often worn when they’re not around, like when you’re in a 1:1 with your manager, a sprint planning meeting, or another environment where someone’s work might be recognized. You might hear about an upcoming project to acquire a new audience and recommend that a budding user researcher take it on, or you’ll suggest to an All Hands meeting organizer that a junior designer should give a talk about a new pattern they’ve introduced to the style guide.

Sponsorship is all about feeling on the hook for getting someone to the next level. As someone’s sponsor, you’ll put their name in the ring for opportunities that will get them the experience and visibility necessary to grow in their role and at the organization. You will put your personal reputation on the line on behalf of the person you’re sponsoring, to help get them visible and developmental assignments. It’s a powerful tool, and the one most effective at helping someone get to the next level (way more so than mentoring or coaching!).

The Center for Talent Innovation routinely measures the career benefits of sponsorship. Their studies have found that when someone has a sponsor, they are way more likely to have access to career-launching work. They’re also more likely to take actions that lead to even more growth and opportunities, like asking their manager for a stretch assignment or a raise.

When you’re in sponsorship mode, think about the different opportunities you have to offer up someone’s name. This might look like:

• giving visible/public recognition (company “shout outs,” having them present a project demo, thanking them in a launch email, giving someone’s manager feedback about their good work);
• assigning stretch tasks and projects that are just beyond their current skill set, to help them grow and have supporting evidence for a future promotion; or
• opening the door for them to write blog posts, give company or conference talks, or contribute open-source work.

Remember that members of underrepresented groups are typically over-mentored, but under-sponsored. These individuals get lots of advice (often unsolicited), coffee outings, and offers to teach them new skills. But it’s much rarer for them to see support that looks like sponsorship.

This isn’t because sponsors intentionally ignore marginalized folks, but because of in-group bias. Because of how our brains (and social networks) work, the people we’re closest to tend to look mostly like us—and we draw from that same pool when we nominate people for projects, for promotions, and for hires. Until I started learning about bias in the workplace, most of the people I sponsored were white, cisgender women, like myself. Since then, I’ve actively worked to sponsor people of color and nonbinary people. It takes effort and intention to combat our default behaviors—but I know you can do it!

Take a look at the daily communications you participate in: your work chat logs, the conversations you have with others, the process for figuring out who should fix a bug or work on a new project, and the processes for making your teams’ work visible (like an architecture review, code review, launch calendar, etc.). You’ll be surprised how many moments there are to sponsor someone throughout an average day. Please put in the time and intention to ensure that you’re sponsoring members of underrepresented groups, too.

This excerpt is from Resilient Management by Lara Hogan, published in June 2019 by A Book Apart. It includes a foreword by Camille Fournier, and is available now as an ebook and paperback. Excerpt copyright © 2019 by Lara Hogan.