Frequently Asked Questions

Most clients start with the free Organizational Clarity Scorecard (takes 5 minutes) to identify where clarity gaps exist. From there, you can schedule a conversation to discuss your specific situation, or jump directly into a Leadership Alignment Session or Organizational Clarity Audit.

You'll receive your results via email with a clarity score across Strategy, Structure, Operations, and People, along with specific recommendations on what to address first.

If you want to discuss what you're seeing or explore working together, you can schedule a conversation. There's no pressure and no follow-up unless you ask for it.

For the Scorecard, immediately — it takes 5 minutes and results are delivered instantly. For fixed engagements (Alignment Session or Audit), we typically schedule within 2-4 weeks depending on availability. For ongoing advisory, we can usually start within a few weeks after an initial conversation.

Fixed-scope engagements range from 5 minutes (Scorecard) to 30 days (Organizational Clarity Audit). Leadership Alignment Sessions are 2 days. Ongoing advisory work typically runs 3–12 months, with some clients working with us for years as clarity needs evolve.

Ongoing advisory is custom-designed based on your needs, cadence, and scope. Most engagements blend embedded strategic support, clarity maintenance, and leadership coaching. Typical engagements range from $10,000–$40,000 per month depending on frequency and complexity. Schedule a conversation to discuss your specific situation and pricing.

Yes. Many clients start with a fixed engagement (Leadership Alignment Session or Organizational Clarity Audit) to address a specific transition or challenge. Some expand into ongoing work, others don't. We're flexible based on your needs.

Yes. For ongoing advisory, we typically bill monthly. For larger fixed engagements, we can structure payment across milestones. We're flexible and can discuss what works best for your budget and procurement process.

A two-day working session (typically in-person or hybrid) with your leadership team to align on priorities, clarify ownership and decision rights, resolve ambiguity, and strengthen team effectiveness. Includes pre-work (stakeholder interviews and context gathering), facilitated workshops, real-time conflict resolution, and a documented clarity framework you can use going forward.

A 30-day diagnostic that maps your organization, identifies where clarity is breaking down, and delivers an actionable blueprint. Includes leadership interviews (typically 10-15 people), org mapping, decision flow analysis, friction point identification, and a comprehensive clarity plan with prioritized recommendations.

We typically work with companies in the 15 to 5,000 employee range, though we've worked with smaller and larger organizations when it makes sense. The real question isn't size — it's whether clarity has become a bottleneck. If you're navigating complexity that comes with growth, transitions, or scale, and execution feels harder than it should, we can probably help. When in doubt, take the Scorecard or schedule a conversation.

Yes. Geography is flexible because we blend in-person and remote work strategically. We're typically onsite for workshops, alignment sessions, and pivotal moments where being in the room matters, then work remotely for ongoing advisory, check-ins, and real-time support. We've worked with companies across North America, Europe, and beyond.

We've worked across SaaS, retail, manufacturing, professional services, healthcare, fintech, and family businesses. Clarity problems are universal — they show up differently by industry, but the underlying patterns are consistent.

Yes. Most clients are companies with 15+ employees where organizational complexity has made clarity a bottleneck, but we've worked with earlier-stage startups navigating pivotal moments — scaling from founder-led to team-led, making first leadership hires, or experiencing rapid growth that's outpacing structure. Take the Scorecard or schedule a conversation to discuss your specific situation.

Yes, though most of our clients are in the private sector. The clarity framework applies across sectors, but pricing and engagement models may differ. Schedule a conversation to discuss your specific situation.

Very. Clarity work requires active leadership engagement — we're not here to deliver reports you'll file away. Expect participation in workshops, regular check-ins, honest conversations about what's not working, and commitment to implementing what we uncover together. The more engaged leadership is, the better the outcomes.

Both, strategically. Being in the room matters for pivotal moments — workshops, alignment sessions, leadership team dynamics, critical transitions, and high-stakes decisions. These are typically in-person.

Ongoing advisory work blends regular remote touchpoints (calls, async communication, real-time support) with periodic onsite visits when presence makes the difference.

The mix depends on your situation, geography, and where you are in the engagement.

Yes, if it's helpful. Many clients ask us to present findings from an Audit or provide Board-level updates during ongoing advisory work. We can also participate in Board strategy sessions or support CEO/COO prep for Board conversations.

We work as embedded advisors, not external consultants. That means being inside your organization, observing how decisions actually get made, identifying where clarity breaks down, and resolving it in real time — not delivering templated frameworks and leaving. We also focus on pattern recognition (seeing what's worked across dozens of companies) rather than process consulting (applying the same methodology everywhere).

If your strategy is sound but execution feels harder than it should — decisions stall, ownership is ambiguous, priorities keep shifting, work gets stuck in coordination loops — that's a clarity problem. If you're unclear on where the business should go or what your competitive positioning should be, that's a strategy problem.

Take the Organizational Clarity Scorecard to see where your specific gaps exist.

Both were founded by Mark Schindler and address related problems. OtterBear focuses on organizational clarity at the company level (working with CEOs, COOs, Boards). The Second Circle Institute focuses on leadership development at the individual and cohort level (working with Directors and VPs making the transition to executive leadership).

Many OtterBear clients send their Directors and VPs to 2CI as part of building leadership capability alongside organizational clarity.

Learn more at the2ci.com.

Email: mark@otterbear.co
Text: 410-371-6704