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Ten(ish) Tips w/ Jeff Diana

October 25, 2021
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An Introduction to Jeff

Jeff is currently the Chief People Officer of Calendly. He has worked as an advisor and investor to many hypergrowth companies, served as the CPO of Atlassian and SuccessFactors, and held leadership roles at Safeco, Microsoft, and GE.

In this series, we talk about why new CPOs should “embrace their newness”, why you should always map out your org chart before starting a new role, and why owning quantitative HR metrics can be so challenging.

- Joseph Quan | CEO & Founder, Knoetic

What advice would you give someone who’s recently become Chief People Officer for the first time?

The advice I’d give to someone new to the job is no different than what I’d give to any other executive.

First, self reflect.  Understand your zone of genius. Know what you’re good and bad at. Know what you need to be successful and know the team you have out on the field. Know the types of skills and styles that are complementary to yours, and the type of people you need to surround yourself with.

Second, embrace your “newness.” It buys you a bit of leeway.  If you don’t know the answer to something, be honest about it, then go out and find the answer. Take advantage of the new-person syndrome. Ask all the “dumb” questions. Don’t hide that it’s your first time in the chair. Don’t be unrealistic and pretend you’ve done it all, especially in the early innings. Otherwise you’re setting yourself up to fail.

Third,  go out and get yourself some great mentors. Find someone who’s done the job before and can fill in your experience gaps. I’m seeing the emergence of all these really great communities for CPOs; these are great places to connect with potential mentors. Find your way into these communities and don’t be afraid to put yourself out there.  Then, make sure you’ve got the right profile and that it’s the right community of people for you. Are these people at a similar stage to you? Are they ahead? There are so many avenues to find a great mentor these days.

[Joseph’s note: I love this idea of embracing your newness, of taking what is often viewed as a weakness and transforming it into a strength. In a new role, we have opportunities to forge personal connections by relying on others and being more open, more vulnerable. For more on this, take a look at Heidi Grant’s work on how leaders can get better at asking for help.]

Find someone who’s done the job before and can fill in your experience gaps. I’m seeing the emergence of all these really great communities for CPOs; these are great places to connect with potential mentors. Find your way into these communities and don’t be afraid to put yourself out there.  Then, make sure you’ve got the right profile and that it’s the right community of people for you. Are these people at a similar stage to you? Are they ahead? There are so many avenues to find a great mentor these days.

If there were a Jeff Diana playbook to building a great relationship with your CEO, what would be in that playbook?

You have to size up the CEO. Really try to understand their drivers, their style, and find the things that they care about to build a strong foundation for your relationship. You have to earn their attention and interest.

How do you do that?

First, you need to understand their style. Every CEO has a different preference. Some want to break bread over dinner. Others expect you to show your vulnerability first before they’ll open up. Others just want you to do the work and deliver on your projects.

A great example of this was my time working at Atlassian with Scott (Scott Farquhar, co-founder & co-CEO of Atlassian). Many CEOs are eager to talk business, financials, and see if you can run fast.

With Scott, he was always intentional about breaking bread. He wanted to do 3-4 hour jam sessions, wanted to know how I grew up, wanted to know my family and my personal values. We’d have a lot of our meetings over meals. He met my wife and kids and I met his family. In doing so, he got to witness this whole other side of me, seeing how I live outside of work. He was gaining confidence in me and the person that he knew me to be.

Second, you need to understand their interests. Don’t be afraid to really dig deep and ask more contemplative questions.

  • What are the things they care about most in life?
  • What type of communication do they like or not like?
  • What’s their mode of processing information?
  • Talk to the executive board member they work with best—how do they work together and what makes it work?
  • What are their personal aspirations and drivers?

After I’ve done all this, I get to the hard work.

Even before accepting or starting a new role, I always begin by building out an org chart. This is sort of a self-preservation tactic to make sure that I’m set up for success in the company. I put this in front of them and I make my intentions clear—are we aligned on the vision and expectation, what we need, and what we’re going to deliver? Once we’ve laid that groundwork, we can start nailing down a concrete business plan.

For example, when I first started working with Lars, CEO at SuccessFactors, he told me how much he cared about people. Knowing this, I laid out the org chart and explained to him what I needed and what comp levels should be set. Soon after, he went to the CFO for 15 minutes and put it into the P&L. Find out what matters to them. Building an org chart is always a great first step for finding potential miscalibrations in your relationship.

The advice I used to get was NOT to do this. There’s the impression that it might spook them off or set the wrong tone. But I like to figure out where there’s misalignment and target that early on. Sure, there’s some things we can debate on like timeframe, business cases, ROI. But we need to be aligned in our visions and expectations in order to make our partnership work.

Working as a CPO or a Head of People, chemistry matters. The HR job is the hardest job at the executive level.  You have peers for sure, but your relationship is unique in that it's your job to take the time to size up your peers, assess them, and give that candid feedback to the CEO and Board.  Even your relationship with the CEO is different than others who report to her/him.  You need to reverse mentor them and in many ways be their leader. That means pushing them and sharing with them your own opinions and expertise. Others don’t get to do that at the same level as we do.

Lastly don’t forget that we are the owners of everything and nothing at the same time. People percentage-wise, we own nothing.  Everyone has a strong opinion on all aspects of our work: culture, people, pay, etc... We have to lead through influence and achieve our agenda through other leaders across the company in order to be successful. We aren’t like the CTO who controls her/his engineers. They can create code and have direct, independent control over outcomes. The People function is not like that.

Working as a CPO or a Head of People, chemistry matters. The HR job is the hardest job at the executive level.  You have peers for sure, but your relationship is unique in that it's your job to take the time to size up your peers, assess them, and give that candid feedback to the CEO and Board.  Even your relationship with the CEO is different than others who report to her/him.  You need to reverse mentor them and in many ways be their leader. That means pushing them and sharing with them your own opinions and expertise. Others don’t get to do that at the same level as we do.

What is the best investment you’ve ever made in your life? Why? (time, money, etc.)  

Perhaps the best investment I made professionally was taking my job at GE (General Electric). This was Jack Welch’s world. I knew I was going to get stretched big time. They had an HR Six Sigma Black Belt job open and they were also looking for HRBPs to join the executive team. I pitched them to give me both jobs.

It wasn’t easy convincing them, but I pushed hard for it. I was about 24 years old at the time, or maybe closer to 23. I tried to convince them a couple different ways. I proved to them that I was a self-starter with raw smarts from my past work experiences that they could depend on to deliver and to juggle multiple projects at once. I made it clear that I was willing and able to work side by side with senior leadership. There was some overlap between the jobs too. I argued that it’d be closer to 1.5 jobs, and ultimately convinced them that I could do both.

Going into a company known for their rapid pace, I saw an overlap within my two positions. I knew it would be a huge commitment, but it accelerated my learning and network 3-4X. Five years later, I’d become levels above what I was when I started and got a job coming out of GE that was beyond what I could’ve imagined at the start.

Getting exposure to Jack Welch was equally valuable, he always pushed me to cover a lot of surface area with brutal honesty and personal integrity. It helped set my approach and commitment to the way I handle C-level jobs.

One thing I learned from working within the intensity of GE—as an executive, it’s easy to lose touch with reality. You have to set guardrails for yourself. Triggers for when you get off path.

One of my guardrails are my kids ( I have 3 amazing sons :) ). I set the goal that I would coach one sport for my kids each season. When I was interviewing with the CEO at  Safeco, I made it clear that the one thing I wouldn’t give up on was that. If you draw these lines and set these guardrails of where you won’t compromise, you’ll know you have balance no matter where you go.

What was a failure that actually set you up for success later in life?

I’ve had many failures. But the one that impacted me the most was a failure I had on the job, working at Safeco. It highlighted that sometimes, our greatest strengths can have negative effects.

When I joined Safeco, I came in as a young, high ego go-getter.  I had a CEO who told me that she wanted to see me set the industry on fire. To do big things. I ended up firing every HR person outside of HQ in my first 30 days of work. I did not do this without research. I met each of these people, and quickly decided that they didn’t have the skill sets we needed for the growth agenda ahead. My mistake-  I didn’t take time to generate buy-in from field leaders before acting or create a replacement plan beforehand. Leaders  wondered what I was doing.

It didn’t take me long to realize my approach was flawed. As always happens,  I wasn’t able to bring in new talent as immediately as I had expected, and that left the remaining team over stretched and temporarily hurt our ability to execute as a business. Even though in the end we massively upgraded our team and our impact, the very aggressive change without finesse was disruptive and unnecessary. A more savvy senior leader would have made that transition more gradually.

I’ve always been quick to process and act. The lesson I learned was that even if you have answers and move fast, the meter for change has nothing to do with you. The ability of an organization to change is not always within our control.

Jumping forward to today, I’ve become someone reliant on building plans and reflecting on processes. I give permission to people to tell me when I’m being an idiot and I ASK for that feedback. Without it, I don’t think I’d be able to grow as much as I did in my career.

Best books that shaped you?

I’m not much of a book person. I’ve always appreciated the early readings of Karl Marx and Engels. Socialists and Marxists are the best capitalists, in my opinion. They understand the alternatives and know how to exploit the system.

Seeing this utopia and what the complete redistribution of wealth would do to the world, they recognize its impracticality and the lack of personal productivity that comes out of it. And knowing this, they understand how to push the line between these drastically different systems.

I also love almost anything about Jack Welch. Jacked Up by Bill Lane is amazing, seeing how he addressed tough issues and brought certain things to importance.

The Goal by Goldratt is also a classic on my list.

[Joseph’s note: If you don’t have time to dig fully into Marx and Engels, I enjoyed this New Yorker piece on what we can learn from Marx about the political economy of the 21st century.]

If books didn’t shape you much, what did?

Watching other leaders in action. Most of my career was informed by GE, and I was lucky enough to watch Jack Welch up close and personal. He taught me amazing things about how to lead and showed me some stylistic things that have fundamentally shaped my personal style.  

Another example is I worked for Rino Piazzola, who did sales at Pepsi. He was a boisterous Italian sales guy running HR and I watched him in meetings often. He placed me in an Organization and Staffing role, which was the #2 spot for heads in HR in large divisions. He told me, “You’ll hate it, but it’ll be the best thing you do”.

He was right. It was all about being a facilitator. Learning that your job is to listen, learn, and influence. You won’t get to drive the company, but the role you play is still wildly important and you won’t learn anything if you don’t stop to listen. We’d do talent reviews regularly, and he’d constantly put his hand on my knee to stop me from engaging. “Your job is not to have an opinion,” he’d tell me. It was about listening more and talking less, which was something I always struggled with. But that experience has always impacted me and I have a great appreciation for it.

What’s bad advice you frequently hear in the people/HR function? Why is it bad? What’s something you believe that few others do in the field?

There’s a philosophy I worry about in the HR field—this idea that our job is to predominantly make others happy. It leads HR pros to the wrong action. It is a bad variant of the concept of servant leadership that leads HR pros to misunderstand our core leadership role.

You often get these signals from across the organization that your purpose is to make people happy. I don’t think that’s my job. My job is making organization as productive as it can be.  If I focus on just making people happy, I’ll create suboptimal outcomes. Making people happy is indeed a noble pursuit, but in my opinion, that is an enabler, not a business outcome.

In that case, how do you think HR teams should measure their efficacy?

The challenge with HR is that it’s hard to come up with quantitative metrics that we own entirely. I tell CEOs all the time, I do not own the attrition rate. I don’t own the people- our leaders do.

What I do own are the tools—the tools needed to put leaders in place and identify root causes and issues. The CMO should technically own their functional attrition and same for other executives in their function.

We need to measure our execution for sure but most importantly, our measures ARE the business measures of ARR growth, cost management, CSAT and more. All other “HR” metrics are intermediate predictors we need to proactively watch and take action but they simply are not the definition of success for our work.

The challenge with HR is that it’s hard to come up with quantitative metrics that we own entirely. I tell CEOs all the time, I do not own the attrition rate. I don’t own the people- our leaders do.

What’s one area where you’re still trying to learn and grow?

I’m constantly trying to learn more about other business functions. I don’t think I’ll ever get deep enough, I’m constantly reminded of how much I have yet to learn from other disciplines.

The second thing is the financials of a business. I aspire to have the same level of depth that CFOs have. Within that, as I work with more startups, I’m trying to understand financing. I’m a neophyte. I’m constantly trying to learn more about what goes into a business from all sides.

I probably do more reading online than I do in my HR positions. I find that getting into positions where I’m exposed to what I need to learn is what pushes me most. Putting myself in environments where I have to learn to be successful helps me continue to grow and become the best I can be.

Joseph Quan, Founder & CEO, Knoetic | CPOHQ

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