How To Prepare for the “Worst Best Job in Tech”

A few of my incredible People Ops teammates, photo courtesy of Sandalwood Photo: https://www.sandalwoodphotoco.com/

Last week, JP Mangalindan wrote an article for Protocol about Chief People Officers, a role he cleverly called “The Worst Best Job in Tech.” If you haven’t read the article, you should consider it. The article documents the ups, downs, and challenges of high-profile Chief People Officers and the roles they assume in a world where employees, candidates, and customers have more information about the inner workings of a company than ever. At a dinner last night, some current MBA students asked me what I thought of the piece and if the “worst best job in tech” is worth pursuing.

The short answer is yes, absolutely. But you should be prepared, so here are five considerations to be mindful of if you’re considering the CPO path in tech:

Respect the Craft: I am a so-called “non-traditional” CPO because I didn’t come from HR or recruiting, so I get a lot of calls from CEOs and founders who say they want to hire a non-traditional CPO because they “hate” traditional HR. I always push back immediately to say that every non-traditional CPO needs to have people with deep experience in employee relations, recruitment, compensation and benefits, learning and development, immigration, and compliance. It’s also worth noting that many HR leaders haven’t worked for companies or leaders who give them the opportunity, training, and latitude to be proactive, so many of the folks blaming HR for not having a “seat at the table” should be giving that feedback to companies and senior executives, too.

It’s totally fine to have a leader from the business run the function, but it can’t be at the expense and dismissal of deep experience in the field. I came into the people field with a deep respect for my colleagues who have spent years learning the ropes, and my job every day is to build a team and a function that combines people who have “seen the movie” in key areas and match that with people we hire from the business and from other fields who can bring new perspective to HubSpot and our team better. So if you’re a former consultant (a frequent profile) or business vertical leader taking on a people role, the most important ingredients to start are empathy and humility — everything else builds on those two qualities.

Do People Work Before It’s In Your Title: The best people leaders I know always showed an interest in and passion for people, even before they worked formally in a people function. So if you’re hoping your CEO will tap you on the shoulder for a people role, you better be the best hiring manager, coach, instructional designer, and coach on your current team. I always tell college students thinking about their careers that the most important thing you can do if you’re switching careers or paths is to “show, not tell.”

The same is true of people leaders — there are always opportunities to refer great people to your organization, volunteer with onboarding, help mentor new hires, or promote your company’s employer brand, and when we look for talent internally, I always look first for individuals who demonstrate their passion for people not just with their words, but with their actions and how they spend their time.

Secure Your Own Life Jacket First: As a Chief People Officer, your most important currency is trust. Leaders have to trust you for great advice. Employees have to trust your ethical compass for big decisions. Candidates must trust that what you are selling is what you deliver each day. Leading any business unit is a grind, but leading a people team is hard because you absorb a lot of emotions from around the organization. Hard terminations. Medical leaves. Illness. Death. People disputes. Ethical decisions around fairness.

If those sound heavy, it’s because they are. One of the best pieces advice I have ever received as a CPO came from a true legend in the field, Russ Campanello of iRobot. He wisely advised me that when you’re running the people function at a growing organization, you need to make sure you have an outlet because you take on a lot. I’m embarrassed to say that when I first heard his advice, I assumed he just meant the quantity of work, but he did not. He meant the heaviness of caring about thousands of people and their families every day and trying to make the right calls when there isn’t a perfect rule book for all of it.

If you want to be a CPO, you need a community of people you can call on and draw on to navigate those decisions, but you also need to really practice and lead the way on self-care and balance — otherwise there’s no way you can absorb the needs of a massive organization and all of its changing needs.

Do Your Homework: People often ask if there is a recommended course of study for people leaders, and the truth is there isn’t. Given that, I always recommend that people consider three forms of homework:

  1. Understand what you don’t know yet: I was lucky enough that our board member, Lorrie Norrington, set me up to spend a day shadowing Ebay’s CPO Kristin Yetto and her leadership team. Doing so taught me a lot, but it also taught me about gaps in my existing knowledge and thought process so I could be more aware of them as HubSpot grew. Some examples (without violating their generosity of time and energy) were the importance of People Analytics (now a prominent and growing function in our org partially thanks to their influences), way more context on how the ops side of a people function scales, geographic nuances in compensation and benefit by level I hadn’t quite anticipated, and a lot of great feedback on what to regionalize versus centralize. The Ebay team didn’t give me the answers, but their incredible team gave me a lot of context to think about how to ask thoughtful questions as we grew, and that’s proven to be invaluable.
  2. Read/watch/listen: It’s not a perfect or exhaustive list by any stretch, but a few things I recommend that people check out if they are considering a people role:
  • Work Rules by Laszlo Bock, The Fearless Organization by Amy Edmonson, and Powerful by Patty McCord are both well known texts in the world of people, and deservedly so — they are worth the read and the admiration and accolades they receive.
  • Julie Zhuo’s work on the Making of a Manager (quick summary here and her full book link here) is really important not just because of its wisdom, but also because of the empathy it creates for first-time managers. One thing you learn early and often in people work is that managers set the tone for the experiences of their team members, so investing in them early and often matters, and I find Julie’s work honest, refreshing, and reflective.
  • You have to know, understand, and do the work yourself on diversity, inclusion, and belonging. So You Want to Talk about Race and Why Are All the Black Kids Sitting Together in the Cafeteria were both really influential for me, and I’m a big fan of Aubrey Blanche (formerly Atlassian, now CultureAmp) and of Khalil Smith at the NeuroLeadership Institute on these topics.
  • First Round Review has the best content online on people stuff in tech by far, so read, follow, and share with your teams.
  • Don’t forget to read CEO/business leader perspectives on people work — a lot of people leaders overindex on reading HR books and miss great business and leadership books with important takeaways for people and culture. I loved Bad Blood (a cautionary tale, of course) because it’s a great example of how the absence of ethics becomes contagious and the bravery of a few whistleblowers. Jack Welch (love him or hate him) was my professor at MIT and his book Winning I come back to often for its sage advice — he was ahead of his time with elevating the people function and in learning and development, so I still have his book on my shelf at home. Don’t just read about cultures that work. I obsess over those that work but also those that failed and the anatomy of what happened — immerse yourself in both so you have a better sense for when things are going off the rails.

3. The final step of homework is internal to your organization. This is just great active listening and making the time and space to do it. Some questions I recommend asking of employees and candidates are:

  • When are you most joyful at work and why?
  • What do you wish our team did more of and why?
  • If you needed help or advice within HubSpot, who would you ask and why?
  • How are you growing personally and professionally here and what could our team do better to support that?
  • What’s the best experience you’ve had with an HR team or recruiter?
  • What was the worst and why?

Internal homework is as important as external homework, and people often skip this step — I recommend not just doing it, but doing it regularly. You’ll identify things you can do better or differently, and heavily inform your roadmap and strategy for the year ahead.

Work on Your Coaching and Communication Skills: Yes, you’re the Chief People Officer, but as you’ve seen from every leaked memo at most high profile tech companies, employee memos and communications (Slack, email, or otherwise) have become the new media leak, so you have to assume that your approach, style, tone, and communications will be external and that you (and your company) can no longer think about “internal communications” as a siloed function .

To that end, people leaders need to get really good and comfortable with large-scale, transparent communication forums (like company meetings, town halls, company-wide emails and announcements) but also really good at coaching senior leaders and giving them tough and kind advice to help them grow. That’s super hard to do, but imperative, and you can’t do it without time, space, and feedback to improve.

Be Exceptional at Receiving Feedback: Like many overachievers, I was good at giving out feedback and not so great at acting on the toughest and hardest feedback to hear. The perfectionist in me even wants to delete that sentence and make it sound better, but it’s the truth. In my early days as CPO, I was so worried about doing something wrong that I talked too much, got too defensive, and shut down when the feedback hit too close to home.

The reality is your team and your organization sets the tone for the leadership team and the company on this issue, so you need to be the best in the organization at not just listening to feedback, but acting on it. Recently, our whole People Ops Leadership team asked for feedback from the business, then each of us signed up to follow up on the feedback and what we are doing about it so we felt personally accountable to do more than listen.

We heard an earful, but our organization and our leadership team were better off for it, so if you want to get the worst best job in tech you have to be willing to accept that sometimes you’re the worst leader in the company and sometimes you’re the best and be able to accept that and improve and grow every day.

Being a Chief People Officer is the most rewarding job I’ve ever had, but it’s also the toughest. I’m delighted that more people are considering people leadership roles, but it’s not for the faint of heart — or faint of feedback. It’s absolutely the best worst job some days, but on the days when it’s the best you are giving people their dream jobs, transforming how people work, and helping your company and its people grow and improve. And that’s worth every worst day along the way, I promise.

*As a note, part of my method for achieving some level of life-work integration is that I no longer take informational coffee chats because I just don’t have time, so the goal with this content is to provide help and guidance (minus the coffee and time). We also documented all of the questions we get more often here.

Chief People Officer at HubSpot. Proud graduate of Bates College, MIT Sloan, and Space Camp. On the interwebs @katieburkie

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