New Rules for Executive Retreats

In his 1967 book “The Effective Executive,” management guru Peter Drucker stated, “Meetings are by definition a concession to deficient organization. For one either meets or one works. One cannot do both at the same time.”

Drucker implored leaders to value time above everything else. “One cannot rent, hire, buy or otherwise obtain more time,” he wrote.

What, then, would Drucker’s assessment be of executive retreats? Would he be more likely to opine that an offsite gathering of senior leaders with the intent to focus on long-term strategy is a necessity or a practice in futility?

There are no statements from Drucker specifically about executive retreats, but parsing his thoughts about strategic planning, meetings, action-oriented leadership and the importance of quiet reflection lead one to believe that he would endorse leadership retreats as long as they are thoughtfully structured and produce actionable ideas.

Drucker felt the value of any meeting – offsite or not – can be measured by what happens once it ends. Actionable commitments should include:

• Who is responsible for the next steps
• What specific actions must be taken
• When those actions need to be completed
• How the results will be monitored and measured

The Conversation Continues

Nearly six decades since “The Effective Executive” was published, the conversation about how executives can most effectively spend their time is ongoing. Regarding executive retreats, we heard similar sentiments to Drucker’s from more than two dozen corporate leaders and entrepreneurs who responded to our questions about the value of these endeavors and how to structure them for optimal benefit.

In their own words, here’s what they had to say.

Are executive retreats worth the investment of time and money?

“Retreats are worth the cost only when they resolve decisions that normal meetings cannot. I build the agenda around three outputs: the few bets we will make; what we will stop; and who owns the next decision. Keep the room to people who can change those choices because observers dilute candor.” – Todd Saunders, founder and CEO of Dalton Mills, provider of an AI operating system for commercial and residential trades

“I measure the ROI by what changes after the retreat, not by how enjoyable the retreat was. If leaders leave with fewer competing priorities, faster decision making and a clearer understanding of who owns what, the cost of a retreat can be small compared with the cost of months of organizational misalignment” – Kristiyan Yankov, co-founder and growth marketer of Above Apex, which provides SaaS-focused link-building and digital PR services

“Are executive retreats worth it? Yes, but not for the reason most leaders think. The value isn’t the agenda; it’s the chance to finally say the thing the team has been avoiding all year. Most leadership teams don’t have a strategy problem; they have an unspoken-conversation problem, and the daily grind never gives them room to surface it. A retreat can.” – Robin Quinn Keehn, founder of People Skillz Education & Consulting 

“Executive retreats are only worth the investment when they solve problems that cannot be resolved effectively through normal meetings. I see the biggest return coming from giving leaders permission to step away from day-to-day firefighting and spend several hours thinking about the bigger questions, including what the company should stop doing, where it should invest more and what opportunities it may be overlooking.” – Pavel Ufimtsev, co-founder Pikadil, a data-driven online savings and e-commerce discount platform

“Retreats are particularly valuable for big-picture strategy, transformation initiatives and priorities that require genuine cross-functional alignment, whether that involves people strategy, funding, revenue, technology or other enterprise-wide implications. Relationship building should not be treated as an afterthought. Dinners, coffee conversations, community service, fireside chats, panels and unstructured time can help create the psychological safety and trust that make collaboration stronger and difficult conversations easier later.” – Ashley Fernandez, executive advisor and keynote speaker

“I test every retreat against one question before I approve the budget. Will this produce a decision we couldn’t have made over email or a normal call? If the honest answer is no, I don’t book it, since our bootstrapped company doesn’t have spare cash for a nice trip that doesn’t earn its cost back. Early on, our retreats looked more like team bonding trips with a loose agenda attached. They felt good in the moment, but nothing changed afterward. Once we started requiring each retreat to end with specific decisions made, not just discussed, the value became obvious immediately. If your team already communicates well remotely, and nothing major needs deciding, a retreat is just an expensive vacation with a company logo on it.” – Nikhil Pai, founder and CEO of Chronicle, an AI-powered SaaS company for Social Security Disability administrators and law firms

“The test I’d apply before anyone books a venue is whether a member of the team can name the specific thing that is stuck. If the honest answer is that morale is low and nobody has said why, then two enjoyable days away won’t change anything because the reason morale is low will still be there on Monday. The retreats that pay for themselves are the ones where a real decision was made in the room and everyone watched it being made, which is something a video call can’t deliver. Most of my clients only see the return six or eight weeks later, so judging a retreat on how people feel in the car park afterwards is a mistake.” – Dan Auerbach, executive coach, Dan Auerbach & Associates

“Executive retreats are worth the investment only if you treat them as designed experiences rather than relocated meetings. Most retreats fail before anyone arrives because the agenda is just the office with better scenery. The ones that pay off are built backward from a question the team cannot answer at its desks. A retreat is the only place a leadership team gets to think together without performing for each other, and that shift is where the real strategic work happens. The ROI isn’t the plan you leave with; it’s the conversations that become possible afterward that weren’t possible before.” – Tony Martignetti, founder of Inspired Purpose Partners and author of “Illuminating Hidden Brilliance”

Your Venue Can’t Be an Afterthought

What constitutes the ideal venue for an executive retreat? For Ben Choder, the site he selected for a team retreat earlier this year provided a palpable aura of leadership from decades past as well as a campus that lent itself to impromptu strolls and meaningful conversations, which can be among the most valuable takeaways from this sort of event.

Choder brought executives from CallRevu, a call tracking platform for the automotive industry, to Windrose on Hudson Learning Center in Ossining, New York.

A landmark in the Hudson Valley (just 45 minutes from New York City), Windrose on Hudson was previously known as Crotonville Conference Center, the retreat built and owned by General Electric. It was used for nearly seven decades to train the company’s top executives and cultivate its corporate culture.

“The best part about doing our retreat at this location was the ghost of Jack Welch and all the people he would fly in haunt the place in a really good way,” Choder said.

He also likes the venue’s 60 acres of outdoor gathering space and 10 miles of biking and walking paths. And the venue’s 200-plus bedrooms are all identical, which, in Choder’s opinion, reinforces the importance of everyone being on equal footing during executive retreats like the one he was part of.

Windrose on Hudson is comfortable without being ostentatious, isolated without feeling isolating – characteristics that others we spoke to for this report agreed are important.

“An executive retreat venue should be sufficiently removed from the normal workplace to change the dynamic, but not so elaborate that the destination becomes the event. Privacy, comfortable working space, easy logistics, minimal distractions and opportunities for informal conversation matter more than luxury,” said Ken Herron, co-founder of VCONify, a software platform that captures data from phone calls, video meetings, chat threads and emails.

Choder also appreciates that Windrose on Hudson offers varied and creative indoor meeting spaces (including an amphitheater and a learning lab) equipped with state-of-the art technology. Creative environments foster creative thinking.

As Tony Martignetti, founder of Inspired Purpose Partners, a leadership and executive coaching firm, told us, “The venue’s job is to interrupt habitual thinking, so the best spaces are ones that disrupt the team’s usual setting. I have run sessions in art museums precisely because standing in front of an unfamiliar object changes how people talk about familiar problems. If the room looks like your boardroom with a better view, expect boardroom conversations.”

What are essential agenda items to maximize ROI of an executive retreat?

“Retreats have shifted from presentation-heavy offsites to working sessions because information can be shared asynchronously.”– Todd Saunders, Dalton Mills

“Keep the agenda focused on a few high-impact topics rather than trying to cover everything.  Business performance, the biggest strategic risks, priorities for the next six to 12 months, resource allocation and decisions that need executive agreement should be at the center, with enough unstructured time for ideas and honest discussion.” – Bogdan Condurache, co-founder of Brizy.io, a “no-code” website builder and page creation platform designed for non-technical users, freelancers and agencies.

“Include an honest review of what is working, what is falling behind and where the business is losing momentum. Then, focus on growth opportunities, customer and market changes, team challenges, and the three or four priorities leadership is willing to protect with real resources.” – Tom Bukevicius, CEO and founder, Scube Marketing

“Treat the agenda like a well-planned project: establish where the business is now; define where it needs to go; identify the biggest obstacles; and agree on who owns each action. I would also include one session specifically focused on what the company should stop doing, because removing low-value work can be just as important as choosing new priorities.” – Thomas Oldham, co-founder UK Construction Blog, a source of news for UK builders, architects, engineers and construction professionals

“Put the hardest conversations near the beginning of the retreat when everyone has the most energy. Review the numbers briefly, then spend most of the time on strategic tradeoffs, customer feedback, competitive threats, major bets and the few decisions where leadership has been stuck.” – Pavel Ufimtsev, Pikadil

“Often, retreats get overloaded and the main point gets lost. Everyone needs a speaking role, or the most senior person wants to do some sort of personal performance evaluation in the moment. Or, someone from X department feels the need to give an update. The most essential items on the agenda are the one or two things that will be decided, who owns the decision, and by when. Groups that skip this spend two days listening to others’ updates and discover on the drive home that nobody said anything. I also think spending time getting an honest read of current conditions – built from what people in the room actually see rather than from hearsay – is very valuable.” – Paul Thallner, founder and principal, High Peaks Group, a business leadership consultancy

“The key is not to over-program the retreat. When every minute is scheduled, leaders do not have enough time to think, discuss issues that warrant depth, or manage the work still happening around them. They leave exhausted with a longer action list instead of clearer decisions and a stronger plan for execution. The best retreats create space for three things that are difficult to do well in the normal cadence of work: deeper strategic thinking, cross-functional alignment, and relationship building. In the senior leadership experiences I’ve designed, some of the most valuable moments came from intentionally using smaller formats, including pod discussions, working sessions, and one-on-one walk-and-talks that paired leaders who might not regularly work together. Those conversations can then be brought back to the broader group, creating more thoughtful discussion than a series of presentations often does.” – Ashley Fernandez, keynote speaker

“Every session on our agenda needs a decision attached to it before it goes on the schedule. Not a topic, not a ‘discussion’ an actual choice the team walks out having made. The agenda mistake I see most founders make is filling the day with updates – the same status reports people could have read in a shared doc beforehand. That’s not what a retreat is for, and it burns the one thing you actually paid for, which is everyone’s attention in the same room at once.

Speaking of that, we cut anything resembling a presentation from our own agenda a couple retreats back. If someone needs to present information rather than debate it, we send it out in advance and start the session already past that step. What’s left is only the conversations that actually needs people in a room together to resolve.” – Nikhil Pai, Chronicle

“The agenda item most teams leave out is the unfinished business between the people in the room. Most senior teams are carrying two or three unspoken disagreements, usually about resourcing or about who actually gets to decide something, and every strategy session sits on top of those. If they are not dealt with early, they leak into every other conversation over the two days. I’d also protect a long block of unstructured time, because the conversations that matter most are often the ones that people won’t start in a facilitated session.” – Dan Auerbach, Dan Auerbach & Associates

“Every offsite agenda I’ve seen circulated the week before starts with a strategy block and ends with a dinner, and the strategy block is where the money goes to die. The version that pays for itself is narrower. You bring the four or five decisions that have been stuck in a Slack thread for a month and you don’t leave the room until each one has an owner and a date.” – Steven Lu, CEO and co-founder of Pin, an AI recruiting platform

“The best agendas balance structured learning with room to breathe. By combining focused connection and genuine downtime, no one becomes a spectator. Build in conversations and small-group discussions that elevate expectations, along with unstructured moments where relationships actually form.

Give attendees some choice, too. Optional activities or flexible blocks can make the experience feel more personal and less prescribed. That mix is where the real return lives. It isn’t about doing more. It’s about doing it meaningfully. Specifically, we’re seeing more intentional white space built into agendas, particularly between daytime programming and evening events. Breakfast functions are often optional, giving attendees the freedom to prioritize sleep, exercise or personal time. Organizations are also becoming more selective about evening programming, focusing on quality over quantity.”  – Ashley Case, senior director of meetings + incentives operations, Cadence Travel

“It can’t be eight hours of agenda. White space needs to happen naturally. There must be opportunities for natural cross-pollination of the teams. Someone from finance gets to spend time with someone from products and someone from tech and someone from marketing. They realize how they all gel together. It gives people more respect for what others are doing in the organization. And if the executive retreat becomes a regular cadence in your company, the first one you do must be drastically different than the second, the third and the fourth.” – Ben Choder, CEO, Submittable, which provides software that thousands of foundations, governments and corporations use to run grant and corporate social responsibility programs

“I work alongside individuals from strategy, design, development, SEO and quality assurance departments. With such a large scope of areas, it becomes quite easy for executives to waste all their time on addressing urgent tasks. The purpose of a retreat is to give executives an opportunity to look at the bigger picture. I would not shy away from bringing up tough issues. Are we servicing the right customers? Does the sales department make promises beyond the capabilities of the team? What areas do we see our people overstretched? The key requirement is simple – you need to return with decisions, owners and deadlines. Otherwise, it will only be an expensive journey.” – James Weiss, managing director, Big Drop Inc., a digital marketing agency

What has changed about executive retreats in the past decade?

“In addition to having a better understanding of how to facilitate meaningful team sessions over the past 10 years, I’ve also witnessed a drastic change in regard to the way executive leadership views filler on an agenda. In the past, senior executives tolerated a great deal of non-productive time during a two-day retreat, including a whole day of team-building activities. Senior leadership now view their time differently and will rapidly disconnect if the agenda appears to be padded. The successful retreats I have recently assisted in facilitating are all short, highly focused and contain purposeful white space. An example of this would be an open afternoon with nothing planned. While it may appear to be risky, I believe that these types of afternoons are when many of the truest and most candid discussions occur – discussions that rarely occur in a formal conference setting.” – Irving Chung, founder and CEO of FranGuidance, an online consulting resource for franchise owners

“The biggest shift is the amount of information leaders have access to before they arrive. Because executives can review dashboards, customer data and reports beforehand, the retreat should not be spent reading presentations aloud. The valuable time is now the discussion around what the data means and what the company should actually do about it.” – Peter Barnett, vice president of product strategy, Action1 Corporation, a cloud-native autonomous endpoint management and patch management platform

“The biggest change is that leaders now need retreats for a different reason – creating space for deep thinking. With remote communication and constant digital notifications, executives can be technically connected all day while rarely having uninterrupted time to think together. The best retreats are becoming less presentation-heavy and more discussion and decision oriented.” – Pavel Ufimtsev, Pikadil

“Teams that talk daily on video calls but rarely share a physical room now use retreats as the actual working session, not the reward trip. The in-person time has to earn its cost differently than it used to. Leadership now expects a retreat to justify itself against a return, the same way any other spend does. A few days of team bonding with no clear outcome is a much harder sell than it was 10 years ago.” – Nikhil Pai, Chronicle

“In-person time has gone from abundant to scarce, which raises the bar. A retreat now has to do what video calls structurally cannot – build trust, surface tension, create shared memory. The old model was information plus recreation; the new mandate is transformation, and executives can feel the difference within the first hour.” – Tony Martignetti, Inspired Purpose Partners

Why Office Space Isn’t the Answer

The current uncertain economic climate has companies seeking ways to cut costs, including possibly bringing an executive retreat in-house. Grant Wycliff, president of Carolina Georgia Sound, a commercial audio, video and surveillance integrator, said that would be a mistake.

Wycliff said he nearly settled for “a conference room and a catered lunch” for his most recent executive retreat, but is glad he didn’t.

“The retreat that we almost held in a conference room would have had the same agenda items – and I initially believed that was OK. But the moment we got out of that building and into a different space, the whole energy shifted,” Wycliff said. “They made eye contact differently, completing each other’s sentences, and even disagreeing out loud instead of nodding along.

“We kept the group to eight people, and I think that was a more important decision than we realized going in,” he added. “Facilitating this small group made it impossible for individuals to hide. The quieter people actually participated in conversations, and we remained on topic instead of branching off into disjointed side discussions, which lead nowhere.

“What really impressed me was an unstructured block we left open on the afternoon schedule. There were no presentations, no slides and all we wrote on a whiteboard was one issue that we had not addressed for some time. I thought we were going to spend 30 minutes on this, so I was shocked when we ended up spending over two hours on it, but walked out with actual decisions.”

This article is from a report on the new look of executive retreats. See the rest of the report here.