Slack’s Kelly Watkins on the Importance of Setting Team Tone Early + More

Kelly Watkins

[Interview] Effective Leadership Tips From Experts

Kelly Watkins is the Vice President, Global Marketing at Slack where she oversees brand, product, platform, and growth marketing. Previously, Kelly led marketing at GitHub and Bugsnag, consulted on brand and marketing strategy for Intel and the Department of Defense, and ran communications at various nonprofit organizations.

We got to know Kelly when she spoke at last year’s FirstMark CMO Summit alongside leaders from Oscar, LogMeIn, Looker, Fanatics & others. Kelly has helped to guide the rocketship that is Slack, and we were eager to learn more about her management style, the lessons she’s learned along the way, and what she’s working on next.

What was your first management role? What did you learn from it?

I first started managing while working in Uganda in 2007. The organization I was with was based in the northern part of the country, which had experienced decades of civil unrest. This made for an intense environment that lacked basic infrastructure for getting programs off the ground.

The biggest thing I learned during this time was how much leaders set the tone for their team, and how things can go off course when this isn’t done intentionally. Teams look to their leaders to calibrate their responses to stress, failure, and adversity, in addition to understanding what celebration looks like. This experience of managing in a fluid context gave me a more well-rounded sense of what management should be — that you can’t just set vision and direction; you also have to tune the emotional frequencies in which people work.

“Teams look to their leaders to calibrate their responses to stress, failure, and adversity, in addition to understanding what celebration looks like.”

Early in your career, before you assumed leadership roles, what was one quality you appreciated in a great manager?

The managers that I’ve most respected and have learned the most from have always been the ones who didn’t pretend they were perfect. They admitted to not knowing answers, apologized for mistakes, and in doing so, invited others to be their partners in the work. There’s nothing more powerful than saying to someone, “I don’t know the answer, but let’s work together to find it.”

I think there’s often a temptation to put on airs when in management and to withhold your shortcomings and feign credibility on any and all matters. People aren’t blind though, and they can tell when you’re bluffing or overstating what you know and what you’re capable of solving. Being human and vulnerable, on the other hand, is invitational and helps people feel like they can contribute to the direction in which you want things to go.

“There’s nothing more powerful than saying to someone, ‘I don’t know the answer, but let’s work together to find it.’”

Is there one moment you can point to that fundamentally shaped your approach to leadership?

In 2008, I took a job at a company called New Profit, where I was in charge of web strategy and digital communication channels. My first project was overhauling their main website, including selecting and implementing a new content management system and building out the frontend of the site with better navigation and content. It was a massive effort and after creating a plan, I sat down with my direct manager, and the partner in charge of marketing and comms to review. What I was proposing needed partner sign off, so this meeting was intended to be a prep session for me presenting the plan to the broader partnership.

Halfway through my presentation, the partner stopped me and gave me direct feedback that I wasn’t ready to meet with the partners. She carefully outlined the gaps between what they would expect to hear and what I had developed, but didn’t stop there. She committed to work with me to get me to a point where the meeting would be a success. The feedback wasn’t easy to hear, but I was able to process it in the best way possible because I had a path to improve *and* a sponsor to help guide the changes I needed to make.

“The feedback wasn’t easy to hear, but I was able to process it in the best way possible because I had a path to improve *and* a sponsor to help guide the changes I needed to make.”

The reason this moment shaped my approach to leadership is that it taught me what investment in someone looks like — that you can’t just point out where they are off course, you have to also commit to helping them get back on track. As a manager, not only is my role to enable my team to thrive, but also it’s to be on the hook for helping people succeed. I learned this from my time at New Profit and it’s the standard I still hold myself to as a leader today.

What framework do you use for your one-on-one meetings?

To keep things organized, I have a private Slack channel with each of my direct reports where we can both post agenda items to discuss in one-on-one meetings. Sometimes something can be solved more quickly in that channel, otherwise we collate all the topics posted each week for in-person discussions.

I view the one-on-one meeting itself as something that should be driven by my directs, as it’s their time and space to raise issues, whether those are about projects or career development. If I have things to discuss or raise, I always save those for the end of the meeting so that the other person has sufficient time for anything that’s on their mind. I also prefer that one-one-one meetings be used for more substantial conversations, rather than status updates, as dedicated time each week is the best opportunity to go deep into topics.

“I prefer that one-one-one meetings be used for substantial conversations rather than status updates.”

On additional tool that I’ve found incredibly valuable is Lara Hogan’s list of questions for a first one-on-one. This information is incredibly valuable to have on hand for the people you work with, as it can guide how you best manage someone and help them thrive. I encourage all managers on my team to ask these questions in their first one-on-ones, and we have set up a custom profile field in Slack that lists each person’s favorite dessert.

What advice would you give to a first-time manager about giving effective feedback?

Giving feedback early and often is one of the most important things you can do as a manager, including both positive feedback about the things someone is doing well, and constructive feedback about areas where someone can improve. However, I often see first-time managers shy away from giving direct feedback out of a fear of not being liked or a concern over hurting someone’s feelings. Avoiding hard conversations ultimately harms the relationships between a manager and their direct reports, so I encourage first-time managers to master *how* to give feedback, as the way in which it is delivered has the biggest impact on how it will be received.

Some “hows” that I think matter most: feedback needs to be shared face-to-face and as part of a dialogue where someone can seek context. After giving feedback, it’s critical to ask clarifying questions like, “What do you hear me saying?” and “How can I best support you as you work through this feedback?” Following up the meeting with the feedback in writing can help someone accurately internalize and reflect on what you said. It’s also important to specify what you expect someone to do next, whether that’s coming up with a plan or making a change by a clear date.

One additional piece of advice I would add is that when giving feedback, it’s important to lead with details about why the feedback is being given in the first place. If someone can understand what’s motivating your feedback, they can better know what to do when you give it.

Have you worked with a coach, and if so, what was the biggest lesson you learned?

I started working with a coach about 18 months ago, and it has been one of the most valuable things I’ve done so far in my career. At the time, I was struggling to reconcile being an introvert and a very private person with the expectations that people have for leaders around being constantly accessible and social. I felt that I needed to intentionally define my leadership style and to do so in a way that was authentic to who I am, otherwise it would not be possible to truly thrive as the leader of a large and growing global organization and in a public-facing role.

The biggest lesson I’ve learned from my coach so far is that we often do things, or take action, in order to have specific results. However, this misses the importance of mindset — that the story in our heads and how we show up in the world fundamentally impact what we do and whether we are successful. Because of this, I find myself spending much more time thinking about my mindset and how I’m being and operating. Checking in consistently on my own headspace informs what I do in positive ways.

What’s one thing you are working on now?

When an organization scales, a leader has to transition from doing the work to getting things done. This isn’t an easy switch for many leaders or their teams, however. Leaders have so much more context about the work given the information they have access to, and they also have opinions on how the work happens and what quality and craftsmanship in execution look like (or at least I do!).

I’ve been thinking about this transition a lot lately and seeking to find ways that I can best equip my team to do their jobs. As a result, I’ve been working on building a structured onboarding program so that everyone who is new has a chance to understand what we do, what we expect, and how to be successful in marketing at Slack. I’ve also been working on how to consistently communicate information out, developing a weekly newsletter/wrap up that I share on Fridays. It covers everything from what’s top of mind and what’s inspiring me to upcoming hires and important dates. Being intentional about sharing this information in a way that everyone has access to helps me move information from my brain into the organization.

Thanks for sharing, Kelly!

Is there someone who you really admire as a leader (not at your current company) that you think would enjoy being interviewed?

Let us know in the comments below.