Step 1 to Leadership Is Accepting You Don’t Have All the Answers: This Manager Shares More

Sponsored by Chronosphere

Rachel Dines

Photo courtesy of Chronosphere.

May 26, 2024 at 12:37AM UTC

Leaders learn by leading, says Rachel Dines, head of product marketing for Chronosphere, a company that she says is redefining monitoring for the cloud-native world.

“I think a lot of people — unfortunately, especially a lot of women — hesitate to throw their hat in the ring for leadership positions because they think that they’re ‘not ready,’ or they’ve been told they’re not ready,” she continues. “Either they think (or have been told) that they don't have enough experience, or that they are waiting to wake up one day and magically have all the knowledge they need to be a leader. This is just another form of imposter syndrome, in my opinion.”

But no one steps into a leadership role with all the answers and, according to Dines, the first step to leading is accepting and understanding that that’s OK. 

“Leaders should be comfortable with not having all the answers and needing to build a team around them that compliments them,” she explains. 

And that’s how Dines has ended up where she is today, leading the product marketing team at Chronosphere after starting her career as an industry analyst, then going to be a product marketing leader at several startups and larger tech companies.

“I love product marketing because it gives you the opportunity to participate in many different areas of the business (especially at a startup!), from product management and engineering, to go-to-market and sales, to finance and even people and talent,” she says. “I also love going deep on a technology, understanding it as thoroughly as I can, so I can translate the technical value propositions into business benefits.”

We caught up with Dines to learn more about her best leadership tips for women. Here’s what she has learned throughout her experience.

Tell us a bit about your job at Chronosphere. 

I usually describe product marketing as the geeky side of marketing — We’re the team that needs to understand the technology and solutions our company sells, so we can make sure that we’re translating the benefits to customers and prospects. Chronosphere offers a SaaS solution that provides site reliability engineering and observability teams end-to-end monitoring across their infrastructure, applications, and business. It’s really exciting to be working at a company that is helping some of the largest consumers of cloud-native get back control over their monitoring. 

How has your day-to-day work changed since you went into leadership at Chronosphere? What about your overall approach to work?

In my previous role, I started as a team of one and over five years grew the team to 10+ people. Now, at Chronosphere, I’m back to running a small team that I plan to grow aggressively over the next several years.

At every phase of company and team size, my role changes quite a bit. While the team is small, I’m very much a “leader/practitioner” (aka player/coach), where I am not only leading the team and setting the longer-term strategy and plans, but I’m also executing a fair amount of the work. I love operating in this model because I really enjoy product marketing fundamentals, and I especially love to build it up from scratch.

As the team and company grows, I get more disciplined with myself about delegation — what tasks that I do today can I teach and empower someone on my team to take over? As the team grows, I get less time doing the product marketing tasks, but I get to spend more time helping my team grow, learn and progress their careers. This is the most rewarding part of being a leader for me: seeing team members grow and take on bigger challenges and hopefully being a positive part of that journey for them.

What’s one strategy you’ve used when managing an individual or team that you think has been particularly effective? 

Listen! Being a good manager and leader is first and foremost being a good listener for your team and teammates. I’m always here to listen to my team’s concerns, complaints, concepts or celebrations about anything in their work (or personal!) life. One key to this is understanding whether the person wants to vent frustrations, work through a problem together or get my advice. I’m not going to jump in and solve everyone’s problems (first of all, I just can’t a lot of the time), but I’m at the very least a sounding board or commiserator. Listening is also good for me because it’s how I learn. This doesn’t come naturally to me because I’m a talker, but I’m working on improving my listening. 

How would you describe your leadership style?  

I’m a fan of the servant-leader style; it’s something that I strive to practice daily. To me, the crux of this philosophy is to think of your role on the team as the unblocker. I’m always trying to find ways to help my team get stuff done, whether that is providing air cover, feedback, cheerleading, prioritizing or something else.

I guess if I had to put a word to my leadership style, I would say “empowering.” I want to give my team members the skills, tools and runway to accomplish their goals.

What’s one strategy you’ve used when managing an individual (or team) that you think has been particularly effective? 

I mentioned delegation earlier. I think this term often gets a bad reputation (i.e., it’s just shoving off tasks that you don’t want to do). The act of delegation, when done right, is both very liberating for me and very empowering for the employee, making it a great management strategy. You know that a major project was effectively delegated when the employee who took it over finds improvements and efficiencies that I never thought of. In other words, if the employee is now running the process or project better than I was, that’s a huge win.

While at Chronosphere, you’ve built a team that you’re now leading. How did you approach this?

My approach to team building is always to look for people with complementary skills and different points of view. Some of the highest achieving teams I’ve built have a wide range of backgrounds, experience levels and skill sets. In the early days, I’m primarily looking for team members who are strong in the areas where I’m weaker. Over time, I look to hire to fill specific gaps and roles. These differences definitely can create a bit of friction on the team, but I actually see that as a good thing. Too much consensus leads to slower teams that produce average results. Great teams have a little bit of conflict, which means that we’re thinking critically and challenging standards.

We’re still in the early days of building the team here at Chronosphere, but growing really quickly. It’s exciting to be here as an early employee knowing we’re going to be a really large organization in the not too distant future.

While building your team, what did you learn that surprised you most? 

No matter how many times I do it, the thing that always surprises me again and again is how hard hiring is. Not the actual process of getting candidates in the door and interviewed, but the part where you figure out what you’re looking for and get everyone on the hiring team aligned on this. Once you know what you’re looking for, then assessing the candidates who come through to determine if they are a good fit is hard during normal business — and 10 times more challenging during the COVID-19 pandemic.

What’s been your most valuable career mistake?

I’ve made the same “mistake” a few times now, which is to join a company where I don’t know a single person. The generally accepted wisdom is to go join companies where you know people already — maybe you’re following a great leader from a past company, or you know a former colleague who works there. This is a great strategy because you have a better understanding of what the job and company will be like.

For some reason, I haven’t been following this advice — I keep joining companies where I don’t know a single person! But this has worked to my advantage because I’ve been lucky enough to find incredible places to work and have expanded my network significantly. I started at Chronosphere without knowing anyone, but in a very short period of time, I’ve managed to build close and trusted work relationships, even though I haven’t met the majority of the team in person! It definitely helps that three-quarters of our current workforce joined during the COVID19 pandemic, so many of us are in the same boat with coming up to speed remotely. Chronosphere offices will start opening again this summer, so I’m looking forward to meeting the team in person.

How do you prioritize and deal with your to-do list each day?

This is a good question because time management is such a challenge! I actually make a list of the tasks or milestones that I hope to accomplish over the course of a week. Then, I look at my upcoming week and try to block off time to get the different tasks done. At the start of the next week, I assess the previous week: what got done, what didn’t and whether things need to roll over to the next week or if other projects now take precedence. Sometimes this works, sometimes it doesn’t, but I find that assessing progress over the course of a week versus a single day is easier to manage.


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