Ep. 137 – Grafana Labs Chief-Operating-Officer, Douglas Hanna

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Becoming a Chief Operating Officer entails a lot of shifting and good relationship building, particularly towards working with the CEO. You need to learn how to work hand in hand and take their vision to reality. In today’s show, Cameron Herold interviews Douglas Hanna, the Chief Operating Officer of Grafana Labs. Having been in a couple of leadership roles, from VP of Zendesk to CEO of Help.com and A Small Orange, Douglas has had his fair share of knowledge, wisdom, and experience when it comes to transitioning from one role to another. He talks about the difference between the entrepreneurial CEO and the entrepreneurial COO and then takes us to his move into the COO role. Going deeper, he shares how he is building on the relationship with the CEO, how he makes his team comfortable with him as a leader, and how he is going up to speed in his new company.

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Douglas Hanna is the COO of Grafana Labs, the company behind leading open-source projects Grafana and Loki and the creator of the first open and composable observability platform. Prior to Grafana Labs, Douglas spent nearly four years as VP Operations at Zendesk. Before Zendesk, he was the Founder and CEO of Help.com, a customer service software company, and the CEO of A Small Orange, the homegrown hosting company. A Small Orange, which Douglas joined in 2010, was acquired by Endurance International Group, the NASDAQ: EIGI in 2012. Douglas continued running the company as SVP and Brand CEO for nearly two years following the acquisition. Douglas earned his Bachelor’s degree in Sociology from Duke University. Douglas, welcome to the show.

Thanks for having me.

I met a guy years ago. We bumped into each other in an airport. We ended up traveling together for seven months through Asia and Australia. For seven months, every single day, he wore a Duke Blue Devils baseball cap. I was this Canadian kid. I didn’t know who Duke was. I came back, and they were all over the final for that year as well. I was like, “I know your alma mater, finally.”

Most people know it for sports. I’m not a huge sports fan, but I did go to a number of games when I was there. It’s a culture, for sure.

That’s part of the culture of the US college system too, getting engaged in that whole part of the system or part of life there. Thank you for doing this. You’ve got a pretty interesting background. There’s a couple of spots that I want to touch on and then dive into Grafana. Before I ask you about the past, why don’t you tell us briefly what Grafana is so we understand because even when I was reading it, I wasn’t entirely sure what a composable observability platform is?

At the simplest level, we help companies and organizations monitor their technical systems. That’s usually what they’re doing. Grafana is an open-source, dashboarding and visualization tool. It makes graphs, charts, and things like that for people. It’s used by individuals and consumers to monitor their home computers and beehives, even to Fortune 500 companies that are usually using it to monitor their servers and other infrastructure. Collectively, that all enable observability around their systems and being able to respond to and address any issues or outages or things that are running the way they’re not supposed to. That’s probably the layman’s explanation. We’ve been scaling that out to be a broader set of offerings over the last couple of years too.

You explained it quite easily. For me to understand it pretty quickly, that was pretty simple. What got you to leave Zendesk? You were at a pretty interesting company, and you were in a pre-senior role there. The CEO of Zendesk was a prior guest on our show. What had you leave Zendesk and go over to Grafana?

I had a great ride at Zendesk. It’s a great company. Our customer at Grafana. I’ve hired a couple of people from Zendesk to come over to Grafana since I joined. I joined Zendesk and there are about 900 people. They’re about 4,000 by the time I left. When a company gets to 4,000 or 5,000 people, it feels like a big company. I’ve spent most of my career in earlier-stage companies. That’s why I think about something else.

A friend of mine who worked in my previous startup had joined Grafana maybe six months before I did. He was telling me about all the traction the company is having and doing these big deals with these interesting companies and open-source projects growing and the team coming together. It intrigued me. I started spending a bunch of time with Raj Dutt, who’s our Cofounder and CEO at Grafana. He brought our team, and it seemed like there was a good fit.

I wanted to be in the COO role personally. When I joined Grafana, there were about 70 people. It was on this venture-backed, high growth trajectory. It super interesting to me personally, and it was a chance to learn about a new space. I barely knew what an observability platform was before I worked here as well. It seemed it was the right mix of team, culture, space, and what I wanted to do and what they needed. The company has grown a ton. It’s been exciting. I was the 72nd employee. We’re a little over 200 now. We’re about to 210.

It goes fast. How much have you raised?

We’ve raised over $75 million. We did about $25 million Series A. The startup time is like a morph of time, for sure. We announced Series B, which is $50 million.

Were you there for the $25 million as well?

I was. That happened shortly after I joined.

I want to dive in around that. What’s it like leaving roles where you in that entrepreneurial zone, leaving the CEO of a couple of companies and moving into a big corporate company like Zendesk? What was that transition like?

It’s a little bit of a learning and adjustment phase, to begin with. My hosting company was acquired by a fairly large company,2,000 or 3,000 people. I was running it as a business unit. I didn’t have to deal a lot with “corporate.” At the time, Zendesk was largely a single product company, one P&L, one set of leaders organized functionally. It was an adjustment. I took a little while to find my footing. The leaders were pretty patient with me.

Over time, post that adjustment period, the startup experience became an advantage. My pace of getting things done and my expectations of like, “We can figure this out later. We can grow and scale as we’re going.” That resonated well with the company. A few companies are like, “We don’t want to get stuff done quickly.” No one is like, “I’d rather let’s go slower, and we do less.” That certainly wasn’t Zendesk.

I was able to leverage the startup skillset and mentality at a big company to get things done quicker and in a way that made sense. It was a good fit for me too. At Zendesk, my background is in and around customer service management. That’s closely related to what they do. There’s a natural fit there too. It was a great experience. At Zendesk, we grew almost 40% a year on the period I was there. That’s still a lot of growth, a big number. They crossed a billion dollars in revenue when I left. That was a super exciting growth stage journey.

Even in any size company, that 40% growth year over year is a fast growth as well. What do you think the difference is between the entrepreneurial CEO and the entrepreneurial COO? Can you describe the differences, behavioral traits, or the types of roles that each play and then how you’ve maybe shifted into more of a COO role?

The COO role appeals to me for a few reasons. One, 0 to 1, is not as exciting to me. I’d much prefer to grow and scale. I like to take something that’s working. We’ll make it better and do more, which has been the journey so far at Grafana. A founder or CEO, they’re usually in that 0 to 1. Raj spent many years with Grafana as a bootstrap company. He and his cofounders, eking it by. We started getting on the trajectory that we’ve been on. That early-stage is not as exciting to me. The CEO coming up with the idea and recognizing the market potential vision. They’re probably more long-term strategy focused. They’re certainly thinking about a mix of technology, product, engineering as well as a go-to-market.

My role is market focused. I’ll frequently say that there are pros and cons of different roles. As a COO, you spend a lot of time thinking about your relationship, rapport, and partnership with the CEO. Hopefully, the CEOs are doing the same thing on the other side of the table. I would imagine it takes up a smaller percentage of their headspace overall because they have a lot of other stuff going on. In many cases, the role maybe a little bit more responsive or reactive to what the CEO wants to do and doesn’t want to do, where they think they’re driving value and where they don’t think they’re driving value. The CEO, you’re leading that dance for the most part, which is their prerogative and it’s great. The CEO role tends to lead. The COO, ideally, is molded around that. There’s are differences and nuances to this, of course, but that’s a more typical pattern.

Grafana Labs: The CEO comes up with the idea and recognizes the market potential vision. They’re more long-term strategy focused. The COO spends a lot of time thinking about their relationship, rapport, and partnership with the CEO.

I like the examples you gave there as well. You talked about the partnership with the COO and the partnership with the CEO. You hope the CEO is as focused on it as the COO. The COO is more focused on it. How do you build a relationship with your CEO? What are the things that you do to keep that relationship strong? Also, what are the things that you do to stay on the same page with their vision for the organization and where they want the company to go?

It’s not a particularly insightful answer. One way is we spend a lot of time together. We’re in a meeting or two a day overlapping. We spend some time one-on-one together. I want to make sure my team has exposure to him and to some of the things he’s working on and thinking about as well. It’s a stay posted on day-to-day things that are happening to the extent they’re relevant, making sure he has the latest forecast, he’s participating in our QBRs and things like that. It’s where we’re at with hiring. Also, we’re talking about strategic things like, “When do we want to raise money? How are we thinking about the M&A we’re doing? What’s our product vision or our go-to-market strategy? How do you get some of the tactical things out of the way so you can focus on the strategic?” That’s how I try and stay on the same page. We’ve done a good job at communicating openly to enable that and to make that possible.

In terms of how we got there, it took some time. Raj and I did not know each other before the hiring process. We didn’t have a pre-existing relationship. We spent a bunch of time together as part of that and a lot of over-communication in the early part until we built some trust and rapport and some things that would have been a conversation between Raj and me. Now, he trusts me to do it. It’s not something we need to spend any time on. It takes patience, trust, and empathy from both parties to get to that part. It’s tough, especially for a founder or a CEO to let go of some things and delegate substantial responsibility to a COO. It’s tough for a COO who’s been used to working with a different type of leader or boss and every person is unique. Tom, who’s my boss at Zendesk and the COO there, is different than Raj. I had to get used to two different styles and personalities as well. I’ve got to a good place.

What do you think it was that Raj saw in you to bring you in as the COO instead of promoting somebody from within?

There is someone on the team who had somewhat a similar function or responsibility to what I have. He’s still on our team. He’s on our customer success function. That person was more of an early-stage builder and less of a scaler. I’m the clearest candidate, internally. He opted out of the role, which made it a low drama situation.

He did opt-out of it.

He didn’t have the title. His direct reports are similar to my direct reports when I joined, if you think about it that way. He was interested in how we grow the company and bring in people who have the experience and some of the expertise to do that. That answers the internal versus external piece. In terms of why me, I had an atypical background. A lot of revenue-focused COOs or salespeople. I’m not a salesperson. I’m more of an operations person, and that appealed to Raj.

I had spent more time in my career on the post-sales side than the pre-sales side, which was interesting to us as we thought about driving customer success and high-quality support. The operating cadence and methods of the company when you think about goal setting, OKRs, planning, was an area that I had a lot of experience in for my time at Zendesk. That was also interesting. That was a fit. I didn’t make the evaluation on behalf of the company. Maybe that’s a better question for our founder or CEO. In our conversations, that’s what came across as well.

When you came in as COO, how long did it take you to get up to speed and get your feet wet and feel you fit in, and you knew the business, and you could start running? Was it 2 weeks, 2 months, 10 months, lunchtime?

It was not that fast. It took a good six months for me to get a firm handle on our space or direction or strategy to build enough rapport with Raj. I felt like I was doing stuff and hiring people and things like that within a couple of weeks. The list of things I did was long in a short amount of time. To feel comfortable and be like, “I got those. I can pitch this to a candidate. I can have intelligent input on what we’re doing from a product strategy direction. I can hold my own with a customer.” That took several months. For people that are making a switch to a new industry, that’s reasonable. As I’ve hired new leaders from other spaces, I’m like, “It’s going to take you 4 to 8 months, an average of six months, to get a handle on all that’s going on and the workspaces because it’s different.”

It’s interesting because we often underestimate how long it’s going to take people. It’ll take you 2 or 3 months to get up to speed. The reality is there’s no way. It’s longer than that. How long did it take for your team to feel comfortable with you? Do you think there was a point where they’re like, “Doug’s got this?”

I’ve done a lot of team building since I joined. If you look at my direct reports, I have hired most of them. The roles didn’t exist in the company. We didn’t have a global sales leader. We didn’t have a marketing leader. We don’t have any ops people. A lot of the folks on my direct team I’ve hired and several of which I’ve worked with before. For the existing people, they’re great at giving me the benefit of the doubt, being excited. I met them during the hiring process. They were onboard quickly. It takes time to build trust and rapport with a new manager and a couple of months to feel like, “I get Doug and how he works and what he’s trying to do.”

I talked to a CEO and he hands all of his new employees the operating manual for himself.

I have something similar to that. I wrote something, it’s called Working with Doug, and I share it with all my direct reports when they get started. It’s pretty straightforward. It covers communication style, how I like to use one-on-ones, what to extract from QBRs and OKRs, and things like that. I get feedback that people think it’s useful. It’s nice to see it all over and out and save yourself a couple of weeks or months of fumbling through those things. I had a new team member start, so I read it to her. I updated it a little bit, but it stayed consistent as my team has grown.

Where did you get the idea for that? You’re only the second person I’ve ever heard doing it.

I read about it somewhere. The one that prompted me to write it was the COO of Stripe. I heard her on a podcast saying that she had something like that. She published a template of it. It’s Claire Hughes Johnson.

It was her who mentioned it in a book, it was a startup handbook or something, and that’s where Matt had read about it. You’re right. That’s consistent with what I’d heard as well.

Claire should get the credit. Have you had her on the show?

I’d love to have her on the show. It’s a brilliant tool. It’s not only vulnerable, it’s smart. The reality is they’re going to get to know you anyway. You may as well fast forward the whole discussion. It’s like, “This is when I’m an asshole. This is when I’m a good guy. This is what pisses me off. This is what doesn’t.” You may as well throw it all in line and go, “Now you’re up to speed.”

I saw a couple of team members of mine create similar ones that they’ve shared with their teams as well. Especially our sales leader, who, in terms of the number of people, has our largest team. In my organization, it’s helpful. If you’re a skip-level manager or more than some of these people, it helps them get a sense of, “Who’s the senior leader? What’s his style? What’s he or she about?”

You said something that I thought was interesting as well, which was you tried to give your team exposure to Raj, to the CEO. How do you try to give them exposure? Do you set up the skip-level meetings or you bring him into meetings with them? How do you do that?

Grafana Labs: The most value-added thing our investors can do on a day-to-day basis is to introduce us to customers and talent.

It’s both. Raj does skip levels. I do skip levels with my team members directly as well on a pretty regular basis. That’s part of our culture, trying to be open and transparent, which are amongst the key values of ours. I try and bring in folks from my team to the meeting. Instead of being the single source of information, I want for Raj to get to know my team members and what their opinions and thoughts are. I’ve hired good people that have a lot of experience and things to add.

We’re in meetings talking about, “Where should we invest in hiring or how do we think about planning for a subsequent quarter.” If that’s a Raj level discussion, I’m happy to bring another to talk about it. The same thing with bringing in team members of mine to our senior leadership team, which is our CEO’s directs. I want them to have exposure to that group, hear their questions and concerns for that group, which is more cross-functional to get to know them as well.

You talked about how long it took you to get up to speed. How did you get up to speed coming into the company? You came in almost having to change the tire on the vehicle as you still keep driving. When you go from 70 to 200, and you had to figure it out as you were going, how did you get up to speed?

I did one-on-ones with everybody on my team, that was about twenty people at the time. I met a bunch of our customers that’s important to me. I asked to join some sales calls and post-sales check-ins and things like that, that’s one of the best ways that a leader can get to know that business. I had this folder on my desktop called Things I Don’t Understand. Let’s say I would come across a deck or a document or something and be like, “I have no idea what this is talking about. I’m not sure what this piece of this is.” I would go through it.

About twice a week for maybe 6 or 8 weeks, I have a tutoring session with one of our product and engineering leaders. Dan, who is patient with me, explained all these things to me, which was immensely helpful. I had a couple of people on my team that had a lot of expertise as well. Dan is a peer of mine. He spent a bunch of time with me patiently. He was trying to educate me on what an open composable observability platform means and our ecosystem, and all these other pieces of what we do. That was immensely helpful.

I was coaching a new hire on my team to do the same. She came from Zendesk as well. We started at the same place I did. I’m like, “Have a list of the things that you don’t get. Make sure you find somebody that will go over them all with you and can help teach you. It will feel academic but it’s useful.” That’s a good thing for anybody that’s in a new space. Whether it’s like, “I don’t understand it technically. I don’t understand what this means. Explain to me why the company does this thing a certain way or not this other way.” That’s a productive conversation. We try to assign every new hire a buddy, including the executive level, who’s a peer, ideally, and who can walk them through. It’s like, “Is this how this is normally done? Is this what I should expect?” Those can be less comfortable conversations with your manager or with someone on your team. We found that the buddy concept works well, even on a senior leadership level.

I like the vulnerability of coming in and going, “I don’t know how this works,” and getting somebody else to explain it versus pretending that you got it all together.

I felt that I was not hired for my technical expertise in the space. I was open about that. It was not hard to look at my resume and tell me that I was not an observability expert. I’ve always felt like I’ve been fairly technical in companies I’ve worked in. This was, by far, the hardest week for me. Coming into Zendesk with a background in customer service, it was not that difficult. Coming into the space having never been a developer or assistant was tough.

I wouldn’t have guessed that either. It would have been impossible for me. Talk about the lessons learned, the two rounds of funding. Your Series A is $25 million, Series B at $50 million. What did you learn in going through those two rounds?

The change has been a strange one in the world. Grafana has been extremely fortunate. The company was bootstrapped for a number of years and decided to raise and had tremendous interest. B round was an inside round. We had the same investor pool and never went out to market with that. That’s not a position that all companies are in. It’s a position that a number of companies and this weirdly hot VC market are in.

For us, we were super fortunate that we were able to be pretty selective on who we want to work with and do so in a way that we thought made sense for our business and what we were trying to achieve. The main lesson learned, especially if you have that luxury of choice, is to spend as much time as you can getting to know your potential investors and understanding what value can they bring beyond the money to your business. For us, the most value-added thing our investors can do on a day-to-day basis is to introduce us to customers and talent, those are the things that we have a limited need for. When we have potential investors reach out to us, we ask for help in those areas and have a fairly compact list of assets that we send to them, and we get their feedback on.

Thinking about how they can help you, VCs tend to be helpful. When they’re pitching you, they may not always be as helpful after that. We’ve had good luck with ours. We can think of a number of people on our team from across the company that we’ve hired as a result of VC introductions and a number of customers that we’ve either made contact with initially or gotten further in the organization with as a result of investor help. That can be meaningful, especially in a B2B enterprise business like we are. If you’re a B2C photo-sharing app which I don’t think there are many of those getting started anymore, that’s maybe less useful on the customer side but definitely on the talent side. If you’re working with a reputable investor, they can bring a lot of clients to that.

Anything that you would do differently, anything in that process that you were like, “We screwed that one up or didn’t do as well as we could have.”

As you’re thinking about fundraising, getting all your ducks in a row administratively is helpful. Thinking about all your employee contracts, agreements, financials, and things that are going to come up in the VC diligence process. If you’re like, “We’re going to raise funding early next year,” and here we are in mid-October, start doing that now. It will save you a lot of time and stress when there’s, hopefully, a million dollar check on the other side of that process. That was in our A round and that was painful. On our B round, it was easy. We learned some lessons. For companies that haven’t done it before, make sure all that stuff is organized. It’s pretty easy to find what a standard VC diligence list looks like. That will be well worth and it eliminates some stress early on.

What about the team-building component? You were good at building teams and building your team. What are the things that you did that helped facilitate that?

I’ve done a lot of hiring since I started here. I color code all my external talent interviews as purple on my calendar. If you scroll back, I have a lot of purple in my calendar, which is great. I recommend that to people. I have a different color for the customer. I have a different color for hiring. It gives you a great snapshot of how you’re spending your time on a given week. We’re weeks away from the end of our quarter. The peach color, which is my customer color, has gotten much denser on my calendar as we get closer to the end of the quarter. That’s expected. On the team-building side, having a vision for what you want your team to end up like. Pick 3, 6, 9, 12 months down the road and where you might want to be opportunistic. Whether I’m talking to our investors or recruiters or other talents, it’s valuable saying, “We’re not looking for B2B person now. We’re looking for someone down the road.” Being opportunistic is valuable.

Is it opportunistic that if you trip over the right person, you might hire them early?

Yeah, exactly. We might collect a roll up or down, depending on who we find. We think is a director-level role, but if I find someone great and they’re more of a VP. Part of being a growing startup is you tend to have that flexibility and that’s important. Another thing I like to do in hiring is I like to meet a bunch of people to calibrate and I’ll tell whether I’m working with a search firm or I’m leading a search myself. I’ll say, “Introduce me to a bunch of people, some that you think we’re not going to be able to get and some that would be below the role, and some that you think are the right fit. I want to calibrate and I want to get a sense of who’s in the market, what good looks like,” etc.

As part of that, I’ll talk to some people. I call people that are a little bit higher, and then I’ll talk to some people that would probably be maybe a little bit below what we would need to be able to compare. That’s an approach that scales across executive hiring down to C-level hiring. You get a sense of who’s in the market. I have some good agencies that I’ve worked with, and we’re able to plug in quickly and that I have relationships with to be able to fill roles. That was useful, too.

Are you guys remote? Are you location-based?

Were remote first. I’m based in San Francisco. I’m in Palm Springs for a little bit of a change of scenery. Raj is based in New York but he’s in Singapore. We’re all over the place. We’re in 31 or 32 countries.

Grafana Labs: There’s this amplification effect of being a senior leader at a company where anything you say, even if it’s off-hand, can be interpreted with 10X the intensity, especially by a lower-level person.

The whole transition during COVID was easy for you because you were already remote.

I used to travel a lot the last 6 or 7 years of my career or more. I haven’t been on a plane in a long time. For someone who’s done a couple of 100,000 miles a year for several years in a row, this has been a big change. We used to get together for a leadership team offsites once a quarter and spend a week locked in a room together. There’s a lot of like, “I wish we were locked in a room for 4 or 5 hours on this.” It would be helpful thinking about things like strategy or pricing or how we think about messaging and some of these other things that are hard to resolve in a 30 or 60-minute Zoom.

How are you doing your remote off sites? Have you started to put systems in place for that?

We do remote off sites at this point, and everyone in the company is taking part in a couple. Our biggest challenge is we have quite a bit of time zone coverage like the US, West Coast, or Europe. About half of our employees are in Europe. We will have usually from 7:00 AM-ish to 11:00 AM-ish Pacific time, which is early morning to late middle-ish evening for our European people. We’ll get everyone together for 4 or 5 hours on Zoom and try to leverage breakout rooms if we can and structure it like you would any other offsite. It’s remote with some breaks. We’ve tried a couple of different things. I had one guy on my team who did an offsite over two weeks, they have an hour a day for two weeks. They’re not going to do that again. We’ve done 3 or 4 days of four-hour sessions. It seems like the sweet spot is maybe 4 or 5 days and three-ish hour sessions, that’s worked well for us given our time zone coverage.

Are there any time zones or regions of the world that are tougher to work with? Do the time zones make it tough? Is it hard to work with people that are based in Bali versus Europe, etc.?

We have a few people in APAC. We’re talking about expanding into APAC much more aggressively, and we’re going to start dealing with this. We’re going to have to get into alternating meetings and how do we think about all hands, especially 95% of our employee base is in Europe and North America. Making the Asia team feel included is going to be hard. That’s part of getting larger as a company and getting more distributed. We’re looking forward to that and forcing ourselves along that way. It’s going to be an adjustment. That’s something we got to do.

We signed a member for the COO Alliance who’s from Kenya and runs a team of about 400 over there. For him, he’s like, “It’s no big deal.” They’re okay with it. The rest of us feel bad that he’s getting up at 2:00 am for his three-hour call with us. He’s like, “I don’t care.” They find it normal. Tell me about your skip-level meetings and how you run those. It seems to be a bit of a science and an art. Some people do them well and some people don’t. I get a sense that you do them well.

I do a decent number of the skip levels consistently. It’s something I do that I enjoy and I find useful. I try to meet every new employee in my organization about 60 to 90 days after they start. I used to be on the rotation on day one or week one. What I found is employees in week one doesn’t know anything. It’s a pleasant chat. We’re not able to talk about what are you seeing from customers? What was your onboarding process like? What’s your manager like? Those questions are much more productive when they know what’s going on.

A strong recommendation, if you’re a COO, don’t meet people in the first week unless it’s pleasantries or a group meeting or something. I have that one-on-one 60- or 90-days in. You’ve also potentially got some data points on them that you can ask about our poke into. For me, when I do skip levels, I like to ask where are their priorities? Are they getting the support and help that they need not only from their manager but from me or maybe the rest of the market or the company’s leadership team? What are they seeing depending on their role? If there are sales leaders who like to skip levels with our sales leaders, it’s like, “What are you seeing with customers? What deals are you worried about?” Things like that.

I spend a bunch of time with customers in my role but I wish I could spend more. I’m interested in our people that talk to customers every day and I feel what those customers are experiencing and feeling. I always ask our support people and our account managers like, “What’s the sentiment of customers? Do they seem genuinely happy? Are they upset? Who’s upset about what?” It’s anecdotal. As an operational, data-driven person, it’s a little silly that I’m asking about these things. I find it interesting that we have all this data. We have a bunch of information on how customers use your product, how they’re transacting with us. I often learned more from talking to a salesperson about how their last deal went. You have to triangulate different things that you hear, of course. It can be useful. For any of our customer-facing folks, I’m always interested in talking about that, too.

They put some color on some of the data. Anything that you would never do in a skip-level meeting? Anything that you’re like, “I shouldn’t have done that. That bit us in the ass. That bit them in the ass.”

These are conversations I have across my team, especially as a COO or some other senior leader is assigning work to the people you’re doing skip levels with. It’s easy for that person to over-index on what their skip-level manager asked them to do. If you aren’t careful about how you frame what you’re asking them to do or how to think about it or what the potential outcome is, it can get dangerous. You might get a question from their manager, your direct report, who’s like, “Did you so and so to do this?” I’d be like, “No, I didn’t.” I would be clear about that. That’s an important nuance of skip level. I try hard that no one hangs up the phone with any homework besides maybe sending me something that they’ve already done or something like that. I don’t want to do that. I’ll usually be intentional like, “Talk to Cameron about that and see what he thinks,” or something like that. I want to put the ball in the court between the employee and the leader and not directly get involved in that.

Another subtlety is to receive the information they’re sharing with us by saying, “That’s interesting or amazing. Thanks for telling me about that.” Not to say, “We have to change that. You’re right. We should fix that.” We don’t know the rest of the story and sometimes their manager does. I got bit in the ass a couple of times where I took their feedback as the entire view of the whole issue and it wasn’t. There was more there on one side. It’s because I said, “Yes, we should fix it,” I’m stuck, and their boss is stuck in between. I screwed that one up a couple of times.

That’s true in any hierarchical communication. If you’re a manager talking to your employee, they’re talking to you about something that’s not necessarily in your control and you’re like, “I agree.” You go talk to your boss and they’re like, “No.” You look stupid and you’ve broken some trust between your employee. “I hear you. Thank you for sharing,” is different from, “I’m going to do something about this.”

It’s subtle but it’s different. What is something you had to work on for your skills as a COO over the years?

Something that I’ve been focused on for a while as a leader is thinking of the empathetic side of leadership. I’m data-driven and operational. I’m like, “Let’s move on as soon as we’ve hit our goal,” and not a whole lot of stop and smell the roses necessarily. I’ve tried to be thoughtful about how I am thanking people authentically for the work that they’re doing and congratulating them on what they’re successful with. Providing feedback has not been a challenge of mine but more so like, “How am I doing?” They feel appreciated and that I’m trying to help them grow versus criticizing. Those soft skills can be tough.

There’s this amplification effect of being a senior leader at a company where anything you say, even if it’s off-hand, can be interpreted with 10X the intensity, especially by a lower-level person. You have to be careful about that. That’s been something I’ve tried to be aware of in all leadership roles I’ve been in. For someone who values direct and open communication, it’s like, “Let me think about how to phrase this in a way where the person will ultimately end up coming away from the conversation feeling great and not beat up or criticized and we can still get to a positive outcome for everybody.” That’s probably something everybody can work on. It’s something I spend time on.

They do take our titles much more seriously than we do as well at times. Doug Hanna, if you were to give yourself some advice when you were 21, 22 years old, finishing at Duke and getting ready to head off in your career, what advice would you give yourself back then that you know to be true now but you maybe didn’t know back then?

The advice I would give any person that’s coming out of school or something is to take on an opportunity that will give you the flexibility to stretch beyond where you think you could be or what you could accomplish. Working at a high growth startup is perfect for that. The company is growing. You’re going to have lots of opportunities. If you’re doing a good job, those opportunities will come to you. You don’t have to actively manage your career nearly as much as you would like at Google or something like that.

People that are coming out of competitive schools like Duke or Stanford or whatever that join Google or Facebook, which are both great companies and comfortable places to work, they’re missing out on a lot of learning potential. You can always go back to those companies. Working at Google for a decade can be a downside to some people that are hiring startups because it’s a unique place, and they’ve been successful. Being successful there doesn’t necessarily translate to being successful in a high growth company.

That’s amazing. Doug Hanna, the COO from Grafana Labs, thanks very much for sharing with us on the show. I appreciate it.

Important Links:

• Grafana Labs
• Help.com
• Zendesk – Employee Engagement And Exceptional Customer Service with Tom Keiser episode

About Douglas Hanna

Grafana Labs is the company behind leading open source projects Grafana and Loki, and the creator of the first open and composable observability platform. 

Prior to Grafana Labs, Douglas spent nearly four years at Zendesk, most recently as VP, Operations at Zendesk. Before Zendesk, he was the founder and CEO of Help.com, a customer service software company, and the CEO of A Small Orange, the homegrown hosting company. 

A Small Orange, which Douglas joined in 2010, was acquired by Endurance International Group (NASDAQ: EIGI) in 2012 and Douglas continued running the company as the SVP and Brand CEO for nearly two years following the acquisition. 

Douglas earned a bachelor’s degree in sociology from Duke University.