Startup Grind
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Startup Grind

A Blueprint for Your Next Management Team Offsite

How to Keep Your Company from Running Off the Rails

In 2015, I joined the management team at Pluralsight, the world’s largest online training library for dev, IT and creative training professionals.

Two weeks into my new role, our team locked ourselves in a windowless hotel board room (next to the beach…just to make it more brutal) for our quarterly management team offsite.

From early morning until late into the night, we talked through key challenges and opportunities facing our business. Three days later, we emerged from the experience with clear strategic company rocks — big meaningful priorities — for the coming quarter.

Our vision was crisp and our relationships were strengthened through the shared experience of hammering through the hard stuff together. Every quarter, our management team offsites provided a consistent opportunity to regroup, reconnect and reflect.

A few days spent at a management team offsite can be just what the doctor ordered to restore your sense of alignment, strengthen your connection to your team, and ensure that you’re not heading off the rails.

When you’re running a company, you’re traveling at a million miles a minute. You’re executing and fighting fires. You’re in the weeds more than you’d like.

Day to day, it’s nearly impossible to helicopter up to a 10,000 foot view to evaluate whether you’re focused on the right priorities. Forget finding time to invest relationships with your peers.

Heading offline for a strategic planning session might seem like an eternity, but a few days spent at a management team offsite can be just what the doctor ordered to restore your sense of alignment, strengthen your connection to your team, and ensure that you’re not heading off the rails.

Set a Cadence & Consider Who to Invite

First-time founder ✌TJ Parker, CEO of PillPack, has raised over $93 million and scaled his company to over 400 employees across the company. An important key to his team’s success?

Communication. TJ recommends quarterly offsites, keeping meetings tightly focused on your senior management team members. It’s up to the CEO to decide who to invite (or not invite).

TJ’s team incorporates a separate Q3 strategic planning session for the coming year as an opportunity to include the next level of leadership below the management team.

Whatever format you choose, plan ahead, get meetings on the calendar, and commit.

Set An Agenda and Leave Time for Conversation

While breaking away from the office for two or three days may feel like a lifetime, chances are time will fly.

To make the most of it, start with a clear agenda that outlines what you hope to achieve, and how you’ll attempt to allocate your time — but leave plenty of time for conversation.

It’s the CEO’s responsibility to drive this meeting. Reach out to your team in advance to understand which topics are high on their lists.

As CEO, you should take the reigns in personally framing the day from the beginning, and encouraging founders to let others do much of the talking.

Don’t stack the agenda — let the conversation flow, but stay focused on the most important items your team needs to solve.

Management teams that let routine agendas dictate their focus abdicate their responsibility to lead. Frequently, the most important things are unexpected and changing. The ability of the team to know and discuss the most impactful things is critical.

— Corey Thomas, CEO, Rapid7

Corey Thomas, CEO of Rapid7 and one of our co-founders, pushes himself and his team to think about the things that they and no one else in the organization can address.

That’s where his executive team spends their time. “Management teams that let routine agendas dictate their focus abdicate their responsibility to lead,” cautions Thomas. “Frequently, the most important things are unexpected and changing.

The ability of the team to know and discuss the most impactful things is critical.” One of the keys to success is agility — adapting to the most important priorities of your organization right now.

Share A Pre-Read

Prepare to prepare. Treat this like a board meeting — make sure your team is able to hit the ground running, by asking each management team member to share any background that’s relevant to the conversation in advance.

Your agenda should dictate which context will be most helpful for you team. This could include the strategic rationale for a new proposed project, new market data, insight from a pricing study or customer development effort.

If you’re planning to discuss specific items to prioritize for the quarter, make sure you have enough context to understand the associated complexity, resources required, and potential impact to the arch of your business.

Gather the materials, and share them with your team, along with the agenda, with at least 48 hours’ notice.

Build Trust

We spend so much time working with people, that sometimes we barely know them — the experiences that have shaped the way they view the world and what motivates them.

One of the things I found most effective about our management team meetings at Pluralsight was that we always kicked off with an exercise aimed at reconnecting us as a team. Sure, we held weekly management team meetings and were constantly in collaboration, but those interactions were all business.

Starting the day focused on each other helped us build trust before we dug into what were sometimes difficult conversations about the future of the organization.

Patrick Lencioni’s The Advantage was particularly helpful to our team as a resource. Lencioni’s Personal Histories exercise is a simple but powerful way to connect with your team on a deeper level.

Personal Histories Exercise

Go around the table and have everyone answer three questions about themselves:

  1. Where did you grow up?
  2. How many siblings do you have and where do you fall in that order?
  3. Describe a unique or interesting challenge or experience from your childhood.

The responses will surprise you. I’ve tried this exercise with several teams, and find that each person’s willingness to open up and share something personal deepens the overall connection of the group, and invites the next person to share something equally personal.

The exercise has helped us understand people’s individual motivations, develop insight about behaviors they exhibit with colleagues, and generally strengthen empathy among the team.

Whatever approach you choose, the goal is to move the focus from your work to your relationships with each other.

Create Clarity

A few weeks ago, we completed our most recent quarterly strategic planning session at Pillar. We use a version of this downloadable Company Playbook adapted from

The Advantage to align around common themes and quarterly objectives. There are plenty of tools and approaches you can use as frameworks for for planning — what’s important is to align around key decisions, actions and ownership.

During the session, our team had plenty of open discussion that veered in interesting directions, but we always made sure to the close the loop with, “What did we decide here?

Which actions will we take? How are we holding ourselves accountable? Who owns delivering against this objective?”

Jeremy Hitchcock, founder and former CEO of Dyn, notes that you should, “Allow for time to let conversations and topics unfold.

If a conflict arises, make sure that there is also a conclusion — there’s a clear decision. Or if there isn’t, talk about what the process is for coming to a decision.”

Just as important as aligning among your management team is aligning outside your core team with senior leaders and your broader company.

Consider a company town hall to share the outcomes of your planning session. Each senior leader should meet with managers on their team to advance to help bring them up to speed and prepare the for clarifying questions that may come from their teams.

Everyone in your company should know what your target looks like, and how they have the ability to impact your core priorities.

Establish Accountability

Each week, we open our Pillar partner by reviewing our progress in a version of this Company Rocks & KPI Dashboard. This simple practice helps us realize very quickly whether we’re spending too much time on “pebbles” vs. “rocks.”

The process helped us see whether major new challenges or opportunities have arisen that are compromising our ability to deliver on what we set out to achieve at the beginning of the quarter.

Make sure that a focus on execution remains front and center. Have a regular “execution” meeting and less regular “strategy” meetings.

— Tom Erickson, CEO, Acquia & Co-Founding Pillar

— Call each other out if you feel like you’re fudging on accountability — if an initiative is “yellow” or “red,” talk about why.

— Are you spending too much energy in the wrong place?

— Has the team hit a seemingly insurmountable obstacle? -

— Do you need your team to help you work through a key challenge?

Don’t Forget to Have Fun

Sure, management offsites can be a critical tool for strategic planning, but they’re also an essential way to relax and strengthen your bond with your team.

We always carved out time to go for a hike, head to the golf course for a fun scramble, or hit the bowling alley for a little friendly competition.

Steve Conine, co-founder of Wayfair, notes that the big value they’ve gotten from management offsites is team building, so they’ve weighted theirs toward casual social events. He and his co-founder, Niraj Shah, typically host.

Steve Conine, co-founder of Wayfair, notes that the big value they’ve gotten from management offsites is team building.

Everyone spends 1–2 nights away together, with most people bunking with co-workers. “Mornings are one hour of big-picture business talk, followed by leisure activities — biking, running, swimming, golf,” he notes.

“Then everyone gets together for lunch, mid afternoon we do wacky team building events (elephant bottle knock-over, build a water bottle rocket contest, build a cardboard boat contest, dodgeball, various relays, packaging contest, leave blower-football race).

Don’t forget to work in time to kick back and enjoy some downtime with your team.

Stepping away from the office will almost always feel like a burden…until you do it. Then you realize that the most valuable aspect of a management offsite is time spent together — time away from the office, away from your computers, away from the pressure of daily work.

How you choose to structure your offsite is entirely in your hands; they key is to carve out the time and make it happen.



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