Startup executive team retreat

Startups Should Have Exec Off-Sites, Too

The week before last, the FullContact exec team went on its first ever “offsite meeting.” I had been fiddling with the idea for awhile, but never made it a priority. It seemed like there was always something better we could be doing with our time.

All companies have infinite ideas and finite resources.

And we had shit to get done.

We had code to sling.

We had sales to make.

We had roadmaps to refine.

We had blog posts to write.

Was an exec off-site really that important? Before the off-site, I would have said: NO. After the off-site, I am now left wondering: Why the hell didn’t we do this sooner?!

To put it in some context, on the first day of the off-site, Ben Deda asked a question that jarred my senses and rocked me to my core:

Do you realize that the last few hours has been the longest we’ve ever spent together?

Ben was referring to the uninterrupted time (or lack thereof) that our exec team had spent together over the past 18 months.

He was spot on. At that moment, I realized that I hadn’t been really leading the execs as a team. I had been leading the team as a collection of individuals. As a result, we were not operating effectively as a team. A collection of very talented individuals can accomplish a great deal. However, they won’t accomplish nearly the amount as those same individuals working as a cohesive team.

The Problem

Prior to the offsite, I thought long and hard about the agenda and how it should be structured. To do this, I thought about the core problem I was looking to solve.

Namely, when all of us were in one-on-one situations, we communicated very freely. But in a group setting, the conversation was much less fluid than I would have liked. It just felt slightly awkward and I couldn’t put my finger on why. If you know me, I like to surface things and get them out in the open (for better or for worse), so it was driving me crazy.

In addition, I found myself as the CEO acting as an information router and I kept wondering – “Why am I relaying this piece of information?  Why is the team not communicating directly?”

I thought that maybe it was simply a matter of familiarity.  Execs running around a startup don’t actually get to spend much time together. Sure, we spend an hour and a half at lunch every week and together in a smattering of meetings.  We also spend way too much time conversing over email.  But those bite-size windows of time are not enough to really get to know one another.

On top of that, since our time at Techstars in 2011, we had added two key additions to the team – Ben Deda (VP of Business Development) and Wim De Pril (VP of Engineering). That changed the co-founder dynamic dramatically but we didn’t really take the time to make sure the new team assimilated Ben and Wim properly and ensure that we all adjusted to our new roles.

So, I put together a plan and an agenda that I thought would help solve the problem.  I’ve copied it verbatim below.

The Agenda

REQUIRED Reading Beforehand:

Wednesday, July 31st – Evening

  • 5:00 PM – Depart Denver

  • 6:30 PM – Arrive in Breckenridge House, Check In

  • 7:00 PM – Get Supplies (i.e. Food and Booze)

  • 8:00 PM – Cook Up Dinner

Thursday, August 1st

  • 6 AM – Hike (Optional)

  • 8:00 AM – Breakfast

  • 9:00 AM – Kickoff – Personal Histories

  • 9:30 AM – Team Assessments

    • Individual Self Assesment

    • Team Assessment of Each Individual

  • 10:30 AM – StrengthsFinder and Peer Evaluation

  • 12:00 PM – Lunch

  • 1:00 PM – Insights, RoundPegg

    • Individual Review and Assessment

    • Team Review and Assessment

  • 4:00 PM Personal Time

  • 7:00 PM – Leave for Dinner

Friday, August 2nd

  • 6:00 AM – Hike

  • 8:00 AM – Breakfast

  • 9:00 AM – Core Values

    • In-Depth Discussion and Decisions

    • Implementation

    • Cascading Messaging

    • Maintenance

  • 12:00 PM – Lunch

  • 1:00 PM – Company Prioritization

  • 4:00 PM – Depart

The Drive Up

Part of what I was trying to achieve was a sense of togetherness for the team.  Given the relatively short 90 minute drive to Breckenridge from Denver, we could have easily had everyone drive up separately. But it was important to me that we do everything together.

So, I decided to spend a little extra money on a rental SUV that could comfortably seat 7 passengers in 3 rows.  With this setup, the 5 of us could easily all travel together. And yes, if we were in some horrific car accident and the entire exec team got killed, we’d all be screwed and so would the company. But hey, we’re a startup, so there’s lots of things that can kill us.

On the drive up, we kept it relatively relaxed.  We talked about work a little, played some music, told some jokes.  It was generally a pretty easy-going vibe.

The House

I had decided to rent a house instead of hotel rooms.   I just think houses are a much different way to spend a couple days compared to a hotel. In a house, there’s common areas like a kitchen, a patio, a living room – you don’t get that in a hotel. Plus, the house is cheaper in the summer time in Breckenridge.

Our house ended up being pretty nice. It had a grill, a hot tub, a sauna, a big theater room, and four bedrooms. We didn’t end up using most of the amenities because we were so busy, but it was nice regardless.

We arrived at the house around 6:30 PM, checked in with the property manager, and claimed some beds.

We were hungry, so we decided to go get food and booze.

The Meals

Over the course of two days, we were to have six meals together – one out in Breckenridge and five in the house. Five meals, five people.

I realized this on the drive up, and I figured it’d be interesting to have each person cook a meal for the team.

So, we drove to the local City Market as we decided who would get which meals. After we arrived, I instructed everyone to go get all the supplies for their respective meals and meet back at the checkout counter in 10 minutes. For the most part, this went pretty smoothly – it only took us 19 minutes to get in and out of the store, with the fixings for five full meals in tow.

I was slotted first to cook that evening, and I grilled bratwursts, steaks and burgers for the team on the outdoor grill. On the menu for the remainder of the trip?  Grilled chicken breasts, breakfast burritos, eggs and bacon, and grilled chicken salad.  Upon reflection, there’s something pretty cool about cooking food for your teammates. Also cool is that we were all pretty good cooks, and the meals were quite tasty.

Day One

We woke up at around 5AM the next day and departed the house at 5:45 AM for a hike. We grabbed some coffee and drove to the hiking trail. The night before, we had decided to hike up to Mohawk Lakes.

I love hiking in the morning, and we had a great time. It was good to get the juices flowing on a 7-mile roundtrip hike – all before 8AM. During the hike, we talked about a lot of things, but also spent a good deal of time quietly enjoying the serenity of the outdoors.

The hike took a little longer than we expected, so we didn’t arrive back until about 9 AM. At that point, famished, we wolfed down breakfast burritos.

At that point, we kicked off the official offsite business. I had decided to roughly follow the format from Five Dysfunctions of a Team, with my own personal twists.

We started by simply talking about ourselves for 5-10 minutes each. Who we were, where we were from, how we grew up, why we were here. Pretty basic stuff, but surprisingly, we all learned a lot about each other that we didn’t know before.

Our exec team tends to be all business, all the time, and sometimes, we can forget to inquire about personal details. This was a good exercise to get us to a certain comfort level before the real hard stuff began.

Next, we ratcheted up the difficulty level.

I asked each person to spend 10 minutes and write down two bullet points about each person, including themselves:

  1. The single biggest strength and contribution to the team
  2. The single thing they could improve the most

After everyone was done, we went around the room and discussed each individual, starting with me.

I went first, and explained what I thought my strengths were (vision, passion, external evangelism and excitement) and my weaknesses (too many starts and initiatives, overestimation of the organizational capabilities and my own ability to get things done).

As we went around, most of the team agreed with my assessment, with a few variances, but we had a candid discussion about each item. We repeated this process for each individual. It wasn’t easy at times, but thankfully, no fist-fights broke out.  It was a very honest discussion, and I was really proud of the team. In addition, each member of the team was acutely self-aware of their own strengths and weaknesses.

Following a short break, we tackled StrengthsFinder.

The premise of StrengthsFinder is to identify the core strengths of an individual, and use those core strengths to help the team, rather than focusing on the weaknesses of an individual. It’s in the assembly of the team that one should focus on balancing strengths from all areas to create an effective team.

We mapped out our strengths as a team, and discussed each one briefly. It was clear that our team was weaker in the ‘Relationship’ category of StrengthsFinder – all business, all the time. This wasn’t surprising to us, but we identified it as something we needed to improve as a group.

After lunch, we worked through RoundPegg and had a broad discussion about our scores versus other teams within the company.  We went deep on several items – particularly communication breakdowns we’ve had in the past, and figured out ways to fix them.

By 4PM, we were mentally exhausted, and it was time for some personal relaxation and reflection time. Some of us cracked open beers to chat and some of us quietly read books. However, all of us ending up catching up on email.

At 7PM, we went out to dinner in Breckenridge. We continued the discussions on a wide array of topics, and had a great meal with terrific conversation. When we returned to the house, someone decided it’d be a great idea to play some Poker. That lasted until way too late into the night.

I found it fascinating to see how different team members played poker – and the styles were aligned with different strengths and weaknesses. For example, as the fund-raiser in chief and the biggest risk-taker, I was a very aggressive poker player. Wim, whose job as VP of Engineering is to ‘keep the trains running on time’ was much, much more conservative.

Eventually, after way too much poker and too many adult beverages, we all turned in. It was a good day.

Day Two

The next day, we ended up skipping the hike, as we all didn’t wake up early enough. Too much late night poker!

We ate breakfast and then started in on a discussion around our core values. Prior to the offsite, I had distributed a Google Doc that we brainstormed what each of our core values were. We had a long list of core values, and the next three hours were dedicated to refining the long list.

We argued.

We debated.

We refined.

We simplified.

We nitpicked word choice.

We were candid with each other about values we couldn’t agree on.

In the end, we distilled it down to a core set of values, listed below.

Our Core Values

  • We Are Customer Focused
  • We Communicate with Candor
  • We Never Stop Improving
  • We Always Keep Shipping
  • We Respect Every Person
  • We Move at the Speed of Trust
  • We Are a Team

I won’t go into depth and detail about these values yet – I’ll do that in another blog post.  However, this was a very valuable exercise to make sure the exec team was on the same page. But getting the exec team on the same page is one thing – getting the entire company on the same page is another matter entirely. So, we devised an approach to communicate these values to the whole team and then mechanisms to continuously monitor and maintain our core values.

For each value, we came up with specific examples and stories from FullContact’s history where we had either exemplified this value or had failed miserably at following the value. We decided that we would communicate these values to the whole company at our next all hands on deck meeting.  Having stories and legends about some of the values helped illustrate the values in real life. For example, I told the story of 126 NOs when it came to “We Never Stop Improving.”

As an exec team, we promised to check up with each other on a monthly basis on our core values.   In each of our retrospectives or weekly staff meetings, we’d have values as an agenda item, to be discussed with candor. Moving forward each month at our all hands, I’d talk in depth about a core value. But most importantly, we all promised each other we’d lead by truly living all the core values – and calling each other out if we slipped up.

Our Working Rhythms

After we defined core values, we moved on to discussing our working rhythms. We had already established a good weekly rhythm, but our weekly meetings weren’t in-depth enough or long enough. We decided to add a monthly in-depth meeting and a quarterly offsite.

Since we have quarterly board meetings, we decided to do the offsite about a week prior to the board meeting so we could all get on the same page, prepare any board materials necessary and have our act together prior to a board meeting. In addition, we already do a monthly all-hands, so we decided to do our monthly exec meetings about a week prior to the all-hands.


It turned out we had to checkout at 1PM, so we didn’t get to go in-depth on company prioritization, but we decided that we’d discuss at our next monthly. We wrapped up our action items and made sure everyone had a clear picture of what they needed to deliver – and by when.

We packed our bags and hit the road.

We  had accomplished a ton in a few short days, but all of us realized that it was just the start.  Building a team that works together in perfect harmony takes a ton of time and effort. But leaving Breckenridge, that’s exactly what we intended to do.

Final Thoughts

I believe our first offsite was a huge success – but only time will tell. I can say with confidence that our employees have received our core values well, and we’re starting to put them into practice. A number of employees have expressed excitement to me that we took the time to craft and define some core values.

Our exec team has been working together in a no-bullshit, straightforward fashion, and I think everyone has a better sense of each other.  In just one short week, I’ve seen improvements.

Scaling technology is hard, but scaling people might be even harder.

So, if you’re busy scaling a startup, make sure to take the time to get away from it all and really get your team on the same page.   The success of your startup could depend on it.

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