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Planning an offsite or workshop? Take this 15 point quiz to see is it will be Breakthrough or Bust.

Teams are disconnected. People are stressed at all-time highs. Many employees have left, been laid off or become disengaged. Leaders need their teams to be healthy, aligned, and in action against clear priorities.

It is time to bring your team together for an offsite or workshop.

Why an offsite or workshop?

Here is typically what we hear:

1) "There are a lot of new people on our team and we need to get aligned"

2) People are stressed, disconnected and disengaged. We need them to bond, feel the love, connect to our vision/culture and give them tools to thrive.

3) "The organization has been through ________________ and we better re-set, transform and grow (fill in the blank with some sort of major shift like lay-offs, resignations, competitive battles, industry disruption, societal disruptions).

4) "It is our annual planning cycle, our regular process is to step back as a team to do forward planning, set priorities, allocate resources, and take the needed time to be strategic, innovate and think together as a team"

5) "My boss said to get the team together for an offsite. Now, what do we do?"

More calls than you would think come to us from reason #5.

For some organizations, this investment of time as a team (whether at the Board-level or team-level) will have huge returns on investment and be a Breakthrough-Boom to their business and teams.

It can result in new energy for the team, clear priorities, team bonding, and new innovative products, services, and processes. Workshops allow teams to identify, understand and openly discuss how they are feeling (especially given how much stress there is in the world They step away from the day to day to explore shifts and opportunities in the marketplace, trends that are disrupting their established approach, changes in their workforce and come out more clearly aligned. They agree on a few sets of major priorities where they can win and develop lists of what they are NOT going to work on anymore.

On the other hand, a workshop can be a Boondoggle or Bust: A boondoggle is defined as "work or activity that is wasteful or pointless but gives the appearance of having value. A painful experience."

For 20 years, we have been designing, facilitating and delivering transformative leadership, strategy, team building, innovation and planning sessions for some of the world's leading organizations. Below are my 15 observations to position for a Breakthrough-Boom workshop and avoid a Boondoggle-Bust.

Take the assessment and see where your organization scores (Boom or Bust?):

◻️ 1. Agree On Priorities:

Are the objectives realistic? Depending on time allocated, what is truly achievable? Most clients try to do about 3-5 times too much at offsites and realize so only as they dig into what is truly needed to win. They often skim the surface, avoid tough choices, and return with the same-ole-same-ole with few transformative actions.

◻️ 2. Pre-Interview, Synthesis and Pre-work:

Do you prepare properly in advance? Are pre-interviews conducted with participants to understand what they see as priorities and to surface any difficult topics the leader may be unaware of? Are the pre-work findings used to accelerate the workshop conversation? Do team members come to the meeting with essential information required to inform the decisions that need to made made?

◻️ 3. Create Clear and Flexible Agenda:

Is a well-structured, yet flexible agenda, shared in advance and actively managed throughout the workshop to reach the objectives? We often tell our clients, being a master workshop facilitator is like being a sherpa for a mountain-climbing team. You need a baseline plan and, based on the weather, conditions, energy, team dynamics, level of excitement, etc., you may modify the approach to ensure your team gets to the top of the mountain, has as much fun as possible and comes down as one victorious team.

◻️ 4. Set Ground Rules and Learn New Tools:

Are clear ground rules set and maintained with self-enforcement by the team itself? Are new tools and techniques learned in the workshop that can be carried back to work for less stress, more focus, more efficiency and better teamwork?

◻️ 5. Invite Participants Selectively:

Are only essential participants invited, regardless of title? We often encourage our clients to keep the group at a size that is highly productive, engaging and value-driving. Inviting too many people due to an "obligation to invite" kills the potential of many workshops.

◻️ 6. Select Proper Workshop Venue for Your Goals:

Is a conducive, comfortable room or venue selected to foster teamwork and trust, strategic thinking, fun, breakouts, creativity, and rich, open dialog?

◻️ 7. Engage Expert, Objective Facilitator:

Do you have a skilled, high-energy, business thought-leader to help design, facilitate and synthesize the offsite so that participants (and the leaders) can focus on the discussion, relationships and outcomes?

◻️ 8. Assure Inclusivity and Variety of Points of View:

Are discussions inclusive of different points of view, not just dominant points of view? Do you bring out the quiet voices and diverse points of view? Do you invite young "non-senior" team members who may bring fresh thinking to your choices?

◻️ 9. Stay On Track and Out of the Weeds:

Does the group stay out of weeds and avoid sidetracks? Do you stay out of the mud, the weeds, the parking lot, the distractions, the pet projects, the "here we go again" rants, etc.

◻️ 10. Force Yourself to Make Key tradeoffs and Decisions:

Does the team force choices and set clear priorities? Does the organization come out with a long list of "No!" items in addition the the "To-do" actions? This is essential. Returning to your teams after an offsite without a "No!" list and more to-dos's is a disservice to their hard work and destroys your credibility.

◻️ 11. Slay Your Dragons (every organization has some):

Are sensitive topics addressed with openness or brushed under the carpet? (stress, culture, interpersonal dysfunctionalities, etc.). If not at this workshop, then when? Some of the biggest breakthroughs we have seen with our clients have been when they were willing to slay their internal dragons and make some difficult choices.

◻️ 12. Bring and Maintain Focus and Energy:

Does the facilitator maintain high-energy and a broad awareness to know when to bring out different people and points of view, take a break, move your bodies, share an inspiring video, etc.

◻️ 13. Set Action Items, Timelines, Names and Accountability:

Are there clear action items, accountability and timelines that come out of the session? Who is putting their name next to each action item as a result of this offsite?

◻️ 14. Clear Plan for Follow Up:

Does the team have a process in place to maintain accountability after the workshop and check progress, troubleshoot (especially for some "No" items sneaking back in) and keep momentum going?

◻️ 15. Prompt, Clear and Inspiring Post-Event Communication:

Does the group generate and communicate outcomes of the workshop promptly, clearly and consistently to the broader organization? We often make explicit time at the end of the workshop to craft the message together for the rest of the organization. We share what we achieved together, the priorities, what we have said "No!" to and what the next steps will be. We recommend the client leadership team send this out before the next business morning to provide inspiration, guidance and priorities before business-as-usual kicks back in.


14-15: Breakthrough! (Your meeting is going to be amazing!)

10-13: Mixed (You need to address several areas to mitigate risks and maximize value)

9 or less: Bust (Your event is in danger of being a Boondoggle-Bust: a waste of valuable time, expense and reputation with your team)

Don't feel bad if you scored lower that you hoped. It is the RARE organization that can bring a senior team together for a workshop to discuss openly, address stress, strategize, prioritize and drive tough decisions. This is where a seasoned master workshop designer and facilitator can be of huge help. Offsites and workshops, are a big investment of your team's already limited time.

That is why orchestras have conductors. Just as it is nearly impossible for a musician to simultaneously play an instrument and be conductor, internal participants cannot remove their personal bias (conscious or unconscious), be contributors and also be the facilitators. Despite the best intentions, often the senior leader and a few voices end up talking the whole time and avoid the tough topics.

Great teams will come out of effective workshops with far greater trust, bonding and alignment. In today's stressed world, this is essential.

If you are planning a workshop or leadership offsite and have any questions, feel free to message me ( to explore your needs. It is amazing when a team comes together and commits to discuss the tough topics, transform, innovate and reinvent how they move forward.

Here is a checklist of the skills Master workshop facilitators have:

  • Quickly establishes trust and credibility with the team

  • Pre-plans deeply based on interviews, hot issues, sensitive topic and the opportunities the teams most excited about.

  • Keeps energy high, focused and fun

  • Synthesizes interview findings into a starting point for the offsite

  • Structures, manages and modifies the agenda in real-time

  • Brings thought-leadership, research and a broad expertise from other clients to be additive in content, process and outcomes

  • Ensures inputs from various participants, not just dominant voices

  • Keeps the team focused on the goals

  • Is objective, honest, asks tough questions and challenges assumptions

  • Ensures accountability and timelines are assigned

  • Forces inevitable tradeoffs

  • Synthesizes and integrate various points of view

Paresh Shah is a globally recognized expert in leadership, strategy, mindfulness and innovation. He is a high energy team builder, trainer, master facilitator, and executive coach. Mr. Shah has worked with executives and Boards around the world to drive strategic and Non-Obvious thinking. Paresh is Co-founder of Lifter Leadership (, a leadership training organization based on his popular TedX talk and forthcoming book: Lifters: Everyday ordinary people who uplift their co-workers, customers, community and company..on purpose. (IdeaPress Publishing 2023)

Paresh is a trained engineer and received his MBA from the Harvard Business School (HBS). He is top rated Leadership Professor in Executive Education and MBA programs and his thinking and insights have been featured in publications such as Forbes, Harvard Business School Publishing,, Inc., Entrepreneur, TedX, Psych Central, Smart CEO, Killer Startups and Under 30 CEO.

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