Mastering Executive Offsites
Too many offsites miss the powerful opportunity to align a leadership team. Here’s how to make yours the exception.
In this episode, Kelly Dwyer, executive coach and facilitator, breaks down what separates transformational offsites from frustrating ones. She’s helped leadership teams at venture and PE-backed companies turn tense conversations into breakthroughs and knows exactly how to keep the “elephant in the room” from derailing trust.
Kelly and host Keith Cowing unpack a tactical playbook: how to prep the right way, design the space for honesty, navigate conflict, and make sure the alignment lasts.
Leaders will walk away knowing how to run an offsite that doesn’t just check a box, but changes how their team thinks, decides, and leads.
00:00 — Why offsites fail (and how to fix them)
02:10 — How prep work sets the tone
05:00 — The value of “having a sleep” between days
07:40 — The CEO’s role: set vision, not the agenda
10:50 — Creating meeting agreements that drive honesty
16:20 — The facilitator’s job: manage time and truth
18:50 — Handling conflict when the “fight” breaks out
22:30 — Tools for structure: parking lots, sticky notes, and timers
25:40 — Decision-making without consensus traps
28:20 — The “Fist to Five” tool for real alignment
30:20 — Ensuring follow-through and lasting impact
33:30 — Why offsites are the most powerful (and risky) meetings you’ll ever run
Follow Kelly Dwyer on LinkedIn: https://www.linkedin.com/in/kellydwyer/
Visit Kelly’s Website: https://kellydwyer.co
Listen to Kelly’s Podcast: https://www.lifefromwithin.com/
Full Transcript
Kelly Dwyer (00:00)
The fight breaks out—and we're not talking about a fist fight. I've never actually been in a meeting with a fist fight, but I have been in meetings where people have started yelling at each other. Well, speaking very passionately...
Keith Cowing (00:01)
Yeah.
As a team, you’ve gotta know all the facts. Being able to draw that out of people and create an environment where they’re comfortable speaking the elephant in the room—if the elephant stays in the room, then the whole team has failed.
Kelly Dwyer (00:21)
It also matters—the level of self-awareness that the CEO has. The CEO has the most power in the room, and whether they choose to use it consciously or subconsciously, they have a CEO card, and they play that card.
Keith Cowing (00:41)
This is Executives Unplugged. I'm Keith Cowing, your host and executive coach, and with me today is Kelly Dwyer.
Kelly is a coach and a facilitator. In addition to one-on-one executive coaching, she facilitates leadership off-sites with CEOs and their leadership teams for venture- and private-equity-backed companies.
In those conversations, she creates an environment to help build trust, generate alignment, and help teams tackle the conversations that really matter.
Off-sites are high-risk endeavors—you could either waste everybody’s time and have the most expensive meeting of the year and come back frustrated, or you could return with your top people excited to work together, aligned, and pointing in the same direction. When that happens, the alignment drips down through the whole company so everyone’s humming together—and nothing is more powerful than that.
That’s what we want you to accomplish, whether you’re a CEO or an operator managing an off-site for your team. So let’s jump in.
Keith Cowing (01:43)
Welcome to Executives Unplugged.
Kelly Dwyer (01:45)
Thank you, Keith. I'm happy to be here.
Keith Cowing (01:47)
So excited to have you on. We're here to talk about off-sites. When you think about CEOs and executive teams—sometimes they’re on-site, sometimes somewhere beautiful, maybe somewhere in between—you can accomplish a lot or completely waste your time. There’s a lot at stake.
We’re here to talk about how to effectively set them up and facilitate them. Let’s just start with a simple one: what makes for a great off-site?
Kelly Dwyer (02:11)
I think a lot of prep. A lot of prep makes for a great off-site.
Even if, when you walk into the room, things have changed in the day or two prior and the agenda goes out the window, the prep is still valuable.
When I say prep—that’s interviews. If I'm doing, say, an annual or quarterly planning off-site for an executive team, I interview all the team members beforehand. Those interviews inform the objectives of the meeting because ultimately, what makes for the best off-site or on-site is that the executives—who are usually the highest-paid people in the company—get the most value from their time together.
I’ll spend 15–30 minutes with each of them. We usually book 30, depending on how much they have to say. I ask: what’s going well at the company, what’s going well with the team, what challenges the company’s facing, what challenges the team’s facing, and what they think the right work is for us to do in the room.
Themes emerge from those interviews that inform the objectives. Now, the meeting sponsor—the CEO—typically has an opinion about what they want the team to focus on.
Keith Cowing (04:00)
The fancy heroes always have opinions.
Kelly Dwyer (04:05)
A mix of the two, yeah.
Keith Cowing (04:07)
Okay, so you’ve got a super-set, a long list, and you’re probably going to have to trim it down and focus. How do you think about the length of the off-site—how many goals you can reasonably accomplish—and how far in advance do you start the prep work?
Kelly Dwyer (04:22)
It depends on the scope.
For long-term strategic planning—say, two to three years out—I might interview people a month to six weeks in advance. For quarterly planning, three weeks before is probably the max, because things change between then and the time we walk into the room, which can impact the agenda.
Keith Cowing (05:00)
Now let’s talk about the space and time. Is it one day? Two days? It’s not one-size-fits-all, but what have you seen work well?
Kelly Dwyer (05:05)
For quarterly planning: a day or a day and a half. If you’ve got a new team member, you may want a day and a half to do the softer, team-building conversations.
If the team’s familiar with one another, a day can work. For annual planning, I’d say two days.
Keith Cowing (05:35)
Yeah, in my experience, one of the most valuable things is having discussions during the day, then dinner—maybe some wine—then sleep. Coming back the next morning, suddenly you’ve got new ideas ready to go.
You can take what came out of day one and attack it with more clarity because everyone’s had time to ruminate. We often don’t have time to think; in reality it’s just bang, bang, execute, execute. This gives you time to think and collaborate in a way you don’t usually get. That overnight can make a big difference.
Kelly Dwyer (06:03)
Right. Yeah, I agree. My mentor calls that “having a sleep.”
We’ll have a sleep in between day one and day two.
I think it’s important to call out that the dinner in between isn’t a “woo-hoo, let’s go rage.” They have to go easy on the alcohol because it impacts their ability to integrate and sleep.
Keith Cowing (06:17)
Yeah.
Kelly Dwyer (06:38)
Now, if they’re early-20s startup people, okay, maybe they can. But…
Keith Cowing (06:42)
I hear you.
I’m picturing a chart with the optimal amount of alcohol at dinner—it’s not zero, it’s not ten drinks—somewhere in the middle where you get conversation and creativity flowing but stay fresh in the morning.
Obviously you don’t need alcohol, and some people don’t drink, which you should respect. But just getting people in an environment where they can loosen up and let things out—it’s valuable.
Kelly Dwyer (07:08)
Right, yeah.
Keith Cowing (07:18)
For people with busy schedules—kids, other life responsibilities—when you truly go off-site and spend a couple of days, the pre-work of scheduling that time is painful. But once you’re there, you can focus.
You just show up at dinner, maybe check a few emails, and the next morning you’re ready to go. That time to mull over what was said and let it ruminate is so important.
If you go straight home, you’re hit with ten other problems and never process what happened. What’s your take?
Kelly Dwyer (07:58)
Yeah, that’s a really good point.
It’s up to the CEO to set that expectation: “I want us to step away.”
It’s not helpful when they’re in the room but still scrambling on email or calls, trying to keep up with everything else. Then they’re exhausted and can’t create mental space.
Keith Cowing (08:31)
Excellent point.
Let’s talk about facilitation in the room from three lenses:
The CEO, setting the stage and tone.
The facilitator—which could be the CEO, chief of staff, or someone like you.
The attendees.
Between those three, what can each do to set up the environment for success or keep things running well?
Kelly Dwyer (09:02)
The objectives have to be clear coming into the room, based on pre-conversations and alignment with the CEO.
Whether you’re an external facilitator like me or an internal one like a chief of staff, the objectives must be clear, and pre-work defined.
Participants should know how to prepare—mentally and logistically. Maybe they complete an organizational health survey. You share the agenda in advance, designed so that if executed well, it helps the team achieve the meeting objectives.
They know what to expect and what the focus is. I always do a warm-up of some kind. It depends on personalities: sometimes something silly and goofy, other times a reflective exercise to prime the brain.
Keith Cowing (10:59)
So jumping in now—you’re running the off-site. What’s the CEO’s job? How would you articulate that?
Kelly Dwyer (11:05)
It depends on the CEO’s personality and team chemistry, but generally their job is to provide their vision—making sure the team is clear on both short-term and long-term direction.
Sometimes it’s a reminder of the long-term vision to ground the conversation.
If there’s a new team member, the CEO’s job may also be to educate—to bring that person up to speed. When these meetings happen early in a new executive’s tenure, it’s a great way to accelerate their learning curve because they’re hearing strategy discussions firsthand.
Keith Cowing (12:15)
Super rich, succinct context dump—here you go.
Kelly Dwyer (12:18)
Exactly. So, vision—yes.
Keith Cowing (12:21)
What does that look like specifically? Slides? Open discussion? Pre-read?
Kelly Dwyer (12:35)
I’ll make the observation explicit: “We have new team members in the room.”
At the start, I take the team through creating meeting agreements—how we’ll work together.
If there’s a new person, I often include “There are no dumb questions” so they feel safe asking basics.
One I like is Step Up, Step Back. In extended leadership teams, some people dominate, others hang back. “Step up” means if you’re usually quiet, contribute earlier. “Step back” means if you talk a lot, speak once, then wait for two or three others before speaking again.
Keith Cowing (14:51)
Love that. People know it intuitively, but if you don’t call it out, they won’t adjust.
Kelly Dwyer (14:59)
Exactly. Another is “Take care of your humanness.”
If we’re off-site, I literally say: here’s where the bathroom is. If you need a break, take it. Need water? Stand up, stretch, walk around. Especially after lunch—it’s hard to sit all afternoon.
Keith Cowing (15:48)
Nobody wants to sit in one room for ten hours. You need dynamic energy. Some breaks are scheduled, others just happen naturally. Sometimes you need to stand up, grab coffee, talk from the corner, move your body.
Kelly Dwyer (16:04)
Yeah. And if you know the team tends to interrupt, add an agreement: don’t interrupt; let people finish their thought. It depends on the team. Sometimes you don’t have the luxury of knowing them well in advance—that’s another story.
Keith Cowing (16:26)
So the CEO sets the tone and vision, gets people up to speed, you set meeting agreements, and everyone’s done their prep.
For those who haven’t worked with an outside facilitator—what’s your role during the day to ensure everything runs smoothly?
Kelly Dwyer (16:54)
My meta-role is to make sure they get maximum value for their time. My job is to help them have the most important conversations.
Ideally those are the objectives we set, but if priorities shift, we reset together. Before diving into a new topic, I’ll ask, “What are we trying to achieve with this conversation?”—so everyone’s clear.
I also manage time, which is an art.
Keith Cowing (17:41)
That’s a brutal one. Everything’s stacked against you when it comes to time.
Kelly Dwyer (17:46)
Yes. Especially if the team is 70% talkers—big thinkers, ideators—that’s hard.
And the CEO’s self-awareness matters a lot. They hold the most power, and whether they wield it consciously or subconsciously, that “CEO card” shapes everything. I quickly learn how the CEO shows up—does it help or hinder moving the conversation forward?
If there’s another dominant personality, I manage that dynamic too.
And yes—when the fight breaks out, it’s not a fist fight, but passionate debate.
Keith Cowing (18:56)
Yeah—it can get contentious.
The point is to get everyone speaking the things that need to be said. One of my favorite meeting agreements: you must speak everything on your mind. Put it all out there. Then we decide what to act on or not.
We can’t have unspoken thoughts. The team needs all the facts and perspectives. Creating that environment—where people feel safe to name the elephant in the room—is key. If the elephant stays, the team’s failed.
Kelly Dwyer (19:34)
Mm-hmm. Yes—that’s the art.
Sometimes I’ll let an argument go for a bit—see if they can manage it themselves. How’s it impacting others in the room? Most of the time, these are seasoned professionals with good emotional intelligence.
Keith Cowing (20:43)
And that’s where a parking lot helps.
We’re not going to solve every issue in the room. Mark it, note where the disagreement lies, and move on. Without dismissing it—because it matters—but the show must go on.
Kelly Dwyer (21:20)
I’m glad you brought that up. “Use the parking lot” is one of my meeting agreements.
I’ll have a wall for it with stickies. It’s not just for disagreements—it’s for rabbit holes.
Sometimes I’ll pause and say, “Hey, time out. This feels like a rabbit hole—should we put it in the parking lot?” Let the team decide. Sometimes they’ll say, “No, we need to keep going.” Okay.
Keith Cowing (22:02)
Do you use timers in the room?
Kelly Dwyer (22:03)
That the team can see? No, not usually.
Keith Cowing (22:07)
I’ve experimented with that and like it—a small timer, set for ten minutes, visible to all. When time’s up, you decide: extend or move on. It forces an active decision.
Sometimes it’s the wrong tool, but it’s helpful.
Kelly Dwyer (22:25)
That’s good. I use one for myself, but not for everyone. I might try that.
Keith Cowing (22:32)
Talking about the room setup—do you like slides? Whiteboards? Sticky notes?
I like whiteboards and stickies—maybe slides for context, but getting away from structure and letting people think and talk openly. Curious what you find effective.
Kelly Dwyer (22:35)
I like that.
It’s a combination—it depends on the work. Generally, I discourage presentations because they eat into dialogue time.
That said, sometimes slides are useful for context—sharing key info that frames a conversation.
Whiteboards are great. I use big wall stickies with smaller ones layered on top—sometimes square, sometimes rectangular. I like voting dots too—it depends on the work.
Usually, when helping a group make decisions, there’s a process: define the question, brainstorm, synthesize, then decide.
Keith Cowing (24:19)
Right—different modes: brainstorming versus synthesis and convergence.
If people are in different modes at once, it’s frustrating.
How do you prime people so the conversation is healthy and everyone’s in the same mode?
Kelly Dwyer (24:47)
I separate brainstorming from synthesis in the agenda—so it’s clear what we’re doing when.
As a facilitator, I’ll say, “Now we’re doing X. You have this much time. Here are your prompts. Use your Sharpie and sticky notes—one thought per sticky.”
Keith Cowing (25:17)
And you’re constrained—you can only fit so much on a sticky with a Sharpie, so you have to be succinct.
Kelly Dwyer (25:23)
Exactly. One thought or idea per sticky—not five micro-notes no one can read from three feet away.
Keith Cowing (25:36)
And on the synthesis side—once you’ve brainstormed, how do you converge? Trim from five ideas to three, make a decision?
Do you like making decisions in the room or assigning follow-ups?
Kelly Dwyer (25:58)
It depends on who’s making the decision.
Are you familiar with the Enneagram? I’m a 9—we love consensus.
Once, I was facilitating and fell into consensus mode, and the CEO stepped in and said, “Hold on. This isn’t a democracy—I’m making this decision.”
So we reframed: everyone rank-ordered the options, then discussed why. The CEO made the call.
If the group’s making the decision, then we decide together.
Keith Cowing (27:27)
That clarity—who makes the call—is crucial.
There’s process (who decides) and content (what to decide). Many teams debate both simultaneously and it gets messy.
Clarify first, then debate the trade-offs. Afterwards, the decision-maker can call it. That’s how you move forward.
Kelly Dwyer (27:58)
Yeah. I also love “Fist to Five.”
Keith Cowing (28:03)
Tell me about that—I’m not familiar.
Kelly Dwyer (28:24)
Fist to Five is a quick consensus gauge. Everyone votes zero to five fingers.
Five: “Best plan ever, fully support.”
Four: “I like it, I’ll advocate for it.”
Three: “Neutral, I’ll go with it.”
Two: “Not my favorite, but I won’t block it.”
One: “Need more information before moving forward.”
Zero: “Fatal flaw—we shouldn’t move forward.”
It gives a sense of how aligned the team is on an idea.
Keith Cowing (29:20)
I love that—and it’s specific.
Often, executives communicate with conviction even on things they don’t care deeply about. You get beneath it and realize it wasn’t a strong opinion.
When you force a zero-to-five, you see the nuance. That’s powerful—not just in off-sites, but in everyday meetings too.
Kelly Dwyer (29:46)
Yes, good point.
Keith Cowing (29:48)
When you dig in like that, it clarifies everything. Excellent tool.
Now—follow-through. You finish the meeting, great discussions, perfect dinner, perfect amount of wine, great snacks, maybe some outdoor activity—everyone’s happy and jazzed.
How do you make sure it doesn’t fall flat afterward? That it leads to real change and people want to do it again?
Kelly Dwyer (30:25)
It depends on my role.
If I’m just facilitating and not meeting with them regularly, the follow-through is on them.
I digitize all outputs and create an action plan. Before leaving the room, we clear the parking lot and review all action items—assigning owners and deadlines.
Within 24 hours, they get the digitized outputs and action plan.
Ideally, they have a cadence of meetings—like an L10 (from EOS): a 90-minute weekly exec meeting with a consistent agenda. Action items roll into that.
If I’m working with an extended leadership team between sessions, we might use a spreadsheet or stoplight tracker—red/yellow/green—tracking progress monthly.
If there’s a chief of staff, that person ensures alignment and accountability between meetings.
Keith Cowing (32:35)
And before you leave the room: review the parking lot, clear takeaways, assign owners, wrap up, digitize.
When they get back, it’s all there.
Kelly, this was super.
If someone’s planning an executive off-site, they now have a playbook: define goals, let the CEO set the tone, clarify roles, set meeting agreements, have a facilitator—internal or external—and ensure good follow-through.
Like you said, this is the most expensive meeting of the year with the most important people in the company. It can either be a total waste or completely change the company’s trajectory.
Where can people find you?
Kelly Dwyer (33:34)
This has been a great conversation, Keith. Thank you for having me.
People can find me on LinkedIn—Kelly Dwyer—or at my website, kellydwyer.co
.
I also have a podcast, Life From Within, which you can find anywhere you listen to podcasts or at lifefromwithin.com
.
Keith Cowing (33:58)
Kelly, thank you so much.
Kelly Dwyer (34:00)
Thanks, Keith.
Keith Cowing (34:01)
I had fun talking to Kelly about off-sites.
I’ve been in many off-sites myself and seen the full spectrum—as both facilitator and participant.
It’s so important to use that precious opportunity to get your team aligned, collaborative, and looking ahead together.
If you enjoyed this, please follow the show, share it with someone planning an off-site, and leave a positive review or comment on your favorite platform.
Until next time—enjoy the ride.
