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“I Used to Think Leadership was a Bunch of BS…” And Other Revelations from HubSpot CEO Brian Halligan

It’s rare that a CEO will be as transparent and candid as Brian Halligan. The CEO and co-founder of HubSpot, an inbound marketing and sales software company based in Cambridge, Massachusetts, isn’t trying to put on airs or be an industry figurehead. Instead, Halligan is doing what comes natural and tweaking along the way.

Voted one of 2017’s Highest Rated CEOs according to reviews by his employees on Glassdoor, Halligan — who moonlights as a Senior Lecturer at the MIT Sloan School of Management — took time away from his to-do list of priorities and the day-to-day demands of being CEO to reveal the truths behind his leadership. What’s the secret sauce? Here’s a hint: staying organized, taking naps and turning up the Grateful Dead. Read on to explore how Halligan has made HubSpot a “hub” of rich company culture.

Glassdoor: What does leadership mean to you?

Brian Halligan: I used to think “leadership” was a bunch of BS.  I yawned my way through my leadership classes at Sloan [Business School].  As we moved HubSpot from startup mode to scale-up mode, I learned how amazingly wrong I was. Every quarter, HubSpot surveys all of its employees and asks them on a scale of 1 to 10 whether they would recommend HubSpot as an employer to a friend (employee Net Promoter Score).  We had a VP whose “score” was dropping fast.  We tried to help that manager and give him feedback, but it kept dropping. Then we replaced the VP with someone new and the score bounced back immediately.  It turned out that leadership mattered and putting a new leader in place not only made the employees happier, but increased that team’s output. This was the real ah-ha moment for me.

Glassdoor: What’s been your most rewarding moment as CEO? Your most challenging?

Brian Halligan: The day after HubSpot’s IPO, we threw a party for our employees at Boston’s Museum of Science. The most rewarding moment was when I stepped across the doorway into the party and saw hundreds of my colleagues there with the biggest smiles on their faces. In those next few moments, I hugged so many HubSpotters and the tears flowed.

That moment was so special to me because so many of our employees had taken a bet on us when they joined HubSpot. When we started, many people didn’t know what HubSpot was or that is was different than HubWay, the Boston bike-sharing company. My co-founder, Dharmesh Shah, has a great saying that, “Success is making those who believed in you look brilliant.” That night this saying came true for me.

Glassdoor: Good leadership is not just one person – How do you work w/ your leaders and management teams to make sure employees have great leadership here?

Brian Halligan: We are investing a ton in this area these days. One unique thing we do is run a program called HubSpot Fellows,  which is essentially a mini-MBA program for employees. You need to apply to the program, and we select a handful of top performers from all of our global offices. The classes are taught by a mixture of real professors from Sloan and  Harvard Business School and our executives. But I think the biggest benefit is that the students get to learn from each other.

Glassdoor: What are some of your productivity hacks or ways that you manage your time?

Brian Halligan: I make a monthly priority list and post it on HubSpot internal wiki for everyone to see.  At the end of the month, I update my status on each priority.  This might not sound earth shaking, but it works for a couple of reasons.  It forces me to really think about my priorities and actually prioritize once a month.  I’ve found this is the right cadence because not enough changes in a week but too much changes in a quarter. By putting my tasks, goals, and results on the wiki, it puts pressure on me to actually perform against them. It sends a signal to the company about what’s on the top of my list.

Another hack I have is that I lean hard into that priority list to drive my daily activity. Many people use incoming Slack messages and emails as an informal priority list.  This way of prioritizing enables you to help everyone else with their priorities, but prevents you from accomplishing your own priorities.  

Lastly, I nap or meditate every day.  A big part of my job is to make good decisions on the important stuff HubSpot’s working on.  By taking time to “calm” my brain down, it enables clarity of thinking and a level of creativity that doesn’t happen when I’m running between meetings.

Glassdoor: In what way do you lean on HR to build the company culture you want?

Brian Halligan: In startup mode, I dramatically under-invested in HR relative to similarly sized companies.  In scale-up mode, I dramatically over-invest in HR relative to similarly sized companies.  

Most companies have someone that is the “voice of the customer.” At HubSpot, we had a woman in our marketing organization, Katie Burke, who was always the “voice of the employee.”  We recently made her our Chief People Officer.  This turned out to be a great call as she is passionate about attracting great talent and developing that talent while they are here at HubSpot.  Those are the two most important priorities that a modern HR organization needs to be great at, in my opinion.

Glassdoor: What are your strategies for dealing with hard days – because even the best leaders have them – and putting on a brave face for the sake of keeping morale high without compromising your humanity?

Brian Halligan: A few hacks:

1.  Naps help.

2.  Calling mom helps.  

3.  I keep a folder with nice notes from employees or ex-employees that I’ll look at if I’m having a bad day.

4.  I vent to my co-founder.  Sometimes it just helps to talk it out and have someone listen to at a minimum and sometimes he has fantastic ideas.  I hit the co-founder jackpot with Dharmesh Shah.

Glassdoor: What does it take to be hired at and succeed at HubSpot?

Brian Halligan: I’m glad I started the company because I don’t think I’d get hired today.  It is a hard place to get a job. You’ve got to be sharp, but equally humble and empathetic. One tip I’d give all applicants is to review HubSpot’s culture code before interviewing and to use the software — we give tons of it away for free.

Glassdoor: What was your first job?

Brian Halligan: I was a paper boy — I delivered the Boston Evening Globe (which no longer exists).

Glassdoor: What’s your morning routine?

Brian Halligan: I’m a night owl….NOT a morning person.  For a long time, I tried to fight this and turn myself into a morning person, but it just didn’t work, so I lean into my night owl-ism.  I probably have had 60 dinner meetings in 2017 and a grand total of 0 breakfast meetings in 2017.

I try to wake up without the alarm.  I turn on some upbeat Grateful Dead music or some classical music if I have something hard to think about.  I eat two hard boiled eggs, some raw vegetables, a handful of blueberries, and a cup of coffee.  Bathe.  Uber to work (that way I can get some work done on the way).

Glassdoor: Share three fun facts about yourself.

Brian Halligan:

1. I have a brutal fear of flying.

2. I just bought Jerry Garcia’s old guitar.

3. I’m obsessed with the Boston Red Sox.

Glassdoor: Grab your smartphone, what’s the last app you opened and what did you do with it?

Brian Halligan: Sorry….really boring…..I just check Instagram.

Glassdoor: What are you doing at 7pm at night, usually?

Brian Halligan: Having dinner at Mistral, a great restaurant in Boston that happens to be in the same building I’ve lived in for the last 17 years.

Glassdoor: If you weren’t a CEO, what would you be (in terms of a job or career)?

Brian Halligan: My dream job would be the general manager of the Boston Red Sox. I was lucky enough to interview the President of the Boston Red Sox, Sam Kennedy, when he came to speak at HubSpot a few weeks ago. I have a lot of respect for this organization.

 

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