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When I was at eBay, Meg was always concerned that I would get hit by a bus. While Meg and I had a great relationship, this wasn’t really out of concern for me; she was concerned that eBay would be left in a lurch and she wanted to ensure there’d be a Maynard Jr. ready to go.

It made for an interesting exercise. Needing to find and train any potential replacements required that I sit down and think about everything I used to run an effective organization. I created a document of questions anyone leading an organization needed to be able to answer.

I’ve become a lot calmer since my years at eBay. (It might have to do with age or it might have to do with not getting awakened in the middle of the night.) But I’ve been sometimes surprised by people who think they’re doing a good job and yet they can’t answer some of the questions I ask. I fear that my response at times was not helpful enough—that perhaps I was not giving out enough tough love. This motivated me to go back to my “Questions” document and edit it for CEOs to help them run their companies better.

These questions are designed to help you get a handle on your business, aggressively deliver the right things today while building for tomorrow, ensure that your plans and approach are understood, and guarantee that your strategy/delivery/performance expectations are in full alignment.

I hope that you find the questions below thought provoking.

How accurate and clear is my strategy and plan?

  • What is our strategy?
  • Is it tested regularly with my team for constant alignment?
  • What does success look like today? Two years from now?
  • What are my objectives & priorities?
  • What trumps what?

Am I effectively prioritizing and making the best decisions for the company (and ultimately for our shareholders)?

  • Are my decisions aligned with the ultimate goals of the company?
  • Am I forcing the right discussions and decisions?
  • Are we working on what’s most important and forcing appropriate trade-offs?
  • Am I a bottleneck to making good and quick decisions?

Am I aiming high enough?

  • What does ‘best in the world’ look like?
    • Volume, speed, quality, cost, ROI
  • Is there anyone else who, in the same circumstances, could do better than me?
  • Is this reflected in my near-term goals? My long-term strategy?
  • Do I hold myself and my organization to the highest level of performance?
  • Are we building capability each quarter so the work that’s being done is easier the next quarter?
  • Am I looking far ahead enough to ensure we build the capability we need in advance so I don’t hold the company back?

Do I have plans to use my org to help create strategic competitive advantages through:

  • Compelling value proposition?
  • High customer satisfaction?
  • Differentiated product?
  • Organizational strength in all key areas (engineering, sales, marketing, etc.)?
  • Beneficial brand differentiation?
  • Competitive barriers to entry?

Am I meeting my commitments?

  • Board commitments
  • Sales targets
  • Product road maps
  • Quarterly deliverables
  • Project deliveries
  • Cost management
  • People management

How effective is my organization today?

  • How is my company perceived within company walls? Outside of them?
  • What is the health of my customer relationships?
  • What is the health of my employee relationships?
  • What is the health of my relationship with my direct reports?
  • What is the health of my relationship with my board?
  • What is the health of my other strategic relationships (suppliers, vendors, press, etc.)?
  • Do I have the right measures in place and are they effective?
    • Am I getting surprised?
    • Are problems identified early?
  • In addition to formal measures, do we leverage intuition to identify issues?
  • Do we resolve problems quickly once they are identified? Do we fix them without impacting our strategic agenda?
  • Are we honest, open and direct about performance and issues—at all levels—in my organization?
  • Are there single points of failure in key processes or knowledge sources?
  • How effective are we at recruiting and retaining high caliber talent?
  • People and culture:
    • Do we manage the “What” and the “How”? (Managing the “What”—execution—is not enough. The “How” is also important. Is the team still standing at the end? Have you used methods that will make it easier next time?)
    • Do I hold myself and my organization accountable for living the values we established?
    • Are we passionate about delighting the customer (both internally and externally)?
  • Are we a can-do organization?
  • Are we always seeking to improve?
  • Are we harder on ourselves than anyone else would be?

Is my future strategy sound?

  • Is it well understood?
  • Is it refreshed regularly?
  • Is it aligned with the board?

Am I on track to deliver against my strategy?

  • Is there appropriate funding in place?
  • Do I have the people I need to pull it off?
  • Will my processes scale?
  • Will my architecture scale?
  • Will my systems scale?

Is my organization prepared for tomorrow?

  • Can I articulate tomorrow’s needs?
  • Are improvement/stretch goals included in the objectives of everyone in my organization?
  • Are employees advancing their skills for tomorrow’s job requirements?
  • Have I properly aligned goals to minimize organizational friction both internal and external to my organization?
  • How hard is it to learn in my organization? (What is the time-to-effectiveness for new hires?)
  • How strong is my talent at the executive level? How committed are they to the company’s mission?
  • Do I have a clear successor?
  • Are there successors for all key roles?
  • As head of the organization, am I growing in the areas I need to?

What threatens my future success?

  • External threats?
  • What is the next big ugly?

What opportunities shouldn’t slip by?

  • Am I pushing innovation?
  • Are we stretching our strategic thinking?
  • Are we surfacing, encouraging, and vetting new ideas at all levels?