The HSS Strategy Roundtable

A half-day for CEOs to pressure-test their strategic thinking with peers.

Eight to twelve CEOs. One day in a room. Real strategic questions worked through with peer perspective and disciplined facilitation. Each attendee leaves with a clearer view of their own situation and a one-on-one read-out from Mark Haas in the week following.

Why this Roundtable, for this moment

Most CEOs don't have a peer group where they can think out loud about strategy. Boards have their own agendas. Direct reports work for them. Peer organizations meet on schedules that don't always match the moment a question is live.

The HSS Strategy Roundtable is built for that gap. It puts a small group of CEOs in a room with a structured method, a neutral facilitator, and the pressure of disciplined work. Each CEO brings a real strategic question they're sitting with. The group probes, challenges, and stress-tests. The output is sharper thinking, peer perspective, and the start of a working logic each CEO takes back to their team.

What changes after the Roundtable

You leave with a clearer view of your strategic question, the assumptions hiding inside your current thinking, and the early shape of a logic you can take to your team. You have peer perspective from CEOs facing parallel questions. You have working artifacts to take home. And you have an individual read-out from Mark to anchor what you learned.

Earned insight

You see your strategic question through other CEOs' eyes. The assumptions you've been treating as facts get probed by peers who have no stake in protecting them. The trade-offs you've been avoiding become visible because the room won't let you avoid them.

Built capability

You leave with practiced fluency in three frameworks most CEOs never use disciplined: the Strategy Choice Map, the "What Would Have to Be True" filter, and a structured stress-test. You won't master them in half a day, but you'll know what they are, what they do, and how to use them on your own strategic questions.

Working artifacts
  • Strategy Choice Map. A one-page tool to anchor your core strategic choices.
  • What Would Have to Be True Worksheet. A template to test your strategic assumptions with evidence.
  • Uncertainty Radar. A visual model for mapping market and internal risks against your strategic choices.
  • CEO Clarity Audit. A short diagnostic to determine whether your current strategy is ready for execution or needs more work.
Individual Read-Out

In the week following the Roundtable, each attendee gets a 30-minute one-on-one call with Mark. He shares his honest read on where your specific situation sits based on what surfaced during the day. This is not a sales call; it's an extension of the work.

How the Roundtable runs

Half a day, in person, structured around five working segments:

  • The Real Problem. Each CEO names the strategic question they're actually wrestling with — not the operational version, the strategic one.
  • The Cascade and Possibilities. The group works through three to five strategic options for a shared case study, then applies the same lens to each CEO's question.
  • What Would Have to Be True. The group probes the assumptions hiding inside the leading direction. What's a fact? What's wishful thinking? What needs evidence?
  • Stress-Test. The chosen logic gets pressure-tested against a simulated disruption — an industry shift, a policy change, a cost shock. Where does it hold? Where does it break?
  • Path to Clarity. Each CEO leaves with a Decision Map: what they'll do in the next 90 days to move from working logic toward a validated strategy.

The cohort is 8-12 senior leaders, CXO level or higher. Mark facilitates. Each CEO contributes a real situation. The group works on shared cases first, then applies the discipline to individual questions. The room is structured so that participants can be candid without competitive friction.

Two formats are available: cross-industry cohorts (broader peer perspective, no competitor concerns) and same-industry cohorts (deeper peer recognition, requires careful curation). The host organization chooses.

What we need from you

A real strategic question. A willingness to think out loud in front of peers. The discipline to bring evidence, not just opinion. Roundtables work because the room is honest. CEOs who come with rehearsed answers don't get the value. CEOs who come ready to be wrong about something walk away with the most.

Pre-work is light: a 30-minute questionnaire two weeks before the session so Mark can prepare. The day itself is full and intense. The post-Roundtable read-out call requires 30 minutes of your time within two weeks of the session.

Fee and logistics

Fee
$2,000 per attendee for the half-day Roundtable, including the post-Roundtable individual read-out call
Cohort size
8-12 senior leaders, CXO or higher (CEOs preferred)
Format
In person, half-day. Full-day version available for peer groups and family offices wanting deeper engagement.
Cohort type
Cross-industry or same-industry — host organization chooses
Lead time
8 weeks from booking to delivery, to allow for venue, pre-work, and follow-up scheduling
Hosting
Hosted at the peer group, conference, or organization's location. HSS-curated cohorts available on request.

The HSS standard

Facilitating a room of CEO peers requires neutrality and authority. Mark Haas is a Certified Management Consultant (CMC) and Fellow of the Institute of Management Consultants USA. He served as Chair and CEO of IMC USA, the U.S. certifying body for management consultants, where he also served as Ethics Officer for 20 years. The Roundtable is run as a neutral third space where CEOs can examine hard truths without competitive friction or political overhead. For more about Mark's background and approach, see About Mark or How I Help.

Common questions

Will I have to share confidential information with competitors?

No. The structure of the Roundtable lets you share your strategic question at the level of detail you choose. Most CEOs find that the discipline of the frameworks lets them work on their real question without revealing competitive specifics. Same-industry cohorts are curated for compatibility before the session.

Is this a sales pitch for HSS engagements?

No. The Roundtable is a standalone product. Some attendees later become PRIME, SPRINT, BUILD, or SYSTEM clients; many don't. Mark's read-out call is an extension of the Roundtable work, not a sales conversation. If a longer engagement makes sense for you, that conversation happens separately.

What if I'm not yet sure what my strategic question is?

That's fine. The pre-work questionnaire helps you frame it before the session. CEOs whose questions are still forming often get the most value because the day clarifies what the real question is.

Can I bring my CFO or COO instead?

The Roundtable is designed for CEOs because the conversations require decision authority. CFOs and COOs are welcome if their CEO is also attending or if the cohort is calibrated for senior leaders below the CEO level. Solo CFO or COO attendance dilutes the dynamic the format depends on.

How is this different from PRIME or SPRINT?

PRIME and SPRINT are private engagements with your own leadership team. The Roundtable is a peer experience with other CEOs. Different work, different value. Some CEOs do the Roundtable first to test the discipline against their thinking, then engage HSS privately for their own team.

If you're a CEO interested in attending, the path is through your peer group, your conference organizer, or directly through HSS for curated cohorts. If you're a peer group leader or conference organizer interested in hosting, see below.

For peer group leaders and conference organizers

If you organize a CEO peer group, family office gathering, or industry CEO summit and want to offer the HSS Strategy Roundtable to your attendees, get in touch. Inquiries are reviewed against fit, audience, and timing. Eight weeks of lead time is required.

Inquire about hosting →