The Importance of Shared Expectations and Staircase Ventures’ “Terms of Engagement”

August 4, 2023

Clear, mutually agreed expectations are the foundation of a strong relationship.


Underpinning any strong relationship is a set of clear, mutually agreed expectations that each party understands and honours.  These expectations reflect values and operating principles; when these are articulated, aligned, and consistently respected, they create strong bonds and deep trust.

Expectations range from day-to-day interactions such as email response time and who takes out the garbage to priorities and values such as how work will be balanced vis-à-vis other obligations and how differences of opinions will be resolved.

Too often, expectations are not clearly defined and as a result, resentment and acrimony builds as people unwittingly act in ways that are inconsistent with how the other person expects them to behave.

By articulating and agreeing upon clear expectations, people can understand what behaviours and approaches they can expect from the other party.  This clarity enables each party to know what the other is anticipating from them, and what they can expect in return.  It also creates a clear agreement that can serve as the basis of discussion when one party believes the other is not delivering on their commitments.

I encourage everyone to establish mutually agreed upon expectations for all their relationships, particularly the most important ones in their home and work lives.


Staircase Ventures’ “Terms of Engagement” provides the foundation of our relationships with our portfolio companies.


At Staircase Ventures, we developed our “Terms of Engagement”, a set of commitments that Staircase Ventures and our portfolio companies agree upon before we make a new investment.  These commitments embody the Staircase Ventures’ values, our founder and portfolio offering, and the expectations that we have of the companies with which we work most closely. 

I am sharing these so potential portfolio companies can understand how we work and the expectations to which we hold our portfolio.  Also sharing it in the hopes that others will be inspired to clearly define and share their commitments and expectations of others, as it is a foundation of a strong, productive, aligned partnership. 


Staircase Ventures Commits to the following for its Portfolio Companies:

Fostering an open, transparent, authentic relationship.

  • Bringing a curious and open mindset to conversations, listening and learning.
  • Delivering honest, empathetic feedback and candidly sharing perspectives and advice.
  • Soliciting honest feedback, valuing it as a gift, and acting upon it with a growth mindset.

Working tirelessly for you, your team, and your company.

  • Responding quickly to emails, texts, and phone calls.
  • Arriving at Board meetings well prepared and ready to discuss key issues.
  • Proactively reaching out with ideas, feedback, and connections.
  • Opening our network for the benefit of the company.
  • Meeting one-on-one with the CEO regularly (as mutually agreed); arriving prepared, focused, and ready to discuss the most important topics.

Offering the 5-pillar Founder Development Platform.

  • Executive coaching: Offer all CEOs the opportunity to work with an executive coach that is a fit for them and their growth objectives for six months within the first year post initial investment.
  • Peer support groups: Offer all founders the opportunity to participate in confidential peer groups with other founders across North America during the first-year post-investment.
  • Health & wellness program: Offer all founders a dedicated, confidential coach, provided by Cleveland Clinic Canada, to help them optimize their mental and physical health in the first-year post-investment.
  • A personal financial advisor: Offer all founders the services of a dedicated financial advisor who specializes in supporting early-stage tech founders.
  • Family stipend: Give all founders a cash stipend to cover unexpected childcare, elder support, or other family needs. This will be paid three months post initial investment.

Sharing Carry amongst the founders in Staircase Ventures Fund I.

  • All founders receive Carry in the fund, as detailed in the Carry LPA.

Ensuring Staircase Advisors are available to support your success.

  • Fostering relationships with world-class start-up/scale-up operators who can help you and your company in different ways.
  • Making introductions to Advisors as appropriate and following up to ensure conversations are relevant and helpful.


Portfolio Companies Commit to:

Fostering an open, transparent, authentic relationship with Staircase Ventures.

  • Sharing updates, both good and bad news, in a prompt, open, honest, transparent manner.
  • Embracing constructive debates and hard discussions.
  • Accepting feedback with a growth mindset.

Building a company culture that values diversity, personal growth, and candid feedback.

  • Proactively seeking to create a diverse team across multiple dimensions including gender, sexual orientation, race, ethnicity, age, experience sets, opinions, and ways of thinking. 
  • Promoting inclusivity that enables the best of each person’s uniqueness to shine.
  • Conducting pulse checks across the company at least quarterly; sharing results with the Board.
  • Providing annual written performance reviews to all employees including 360-degree feedback.
  • Welcoming an annual written performance review of the CEO, conducted by Staircase Ventures Managing Partner (or other Board member), which includes 360-degree feedback.

Operating the company based on a clear strategy, operating plan, budget and KPIs.

  • Sharing detailed financials – including actuals vs projections and revised forecast (if applicable) monthly in Excel or Google Sheets.
  • Reporting monthly on progress vs objectives on key initiatives and KPIs, learnings, challenges, and plans to address any shortfalls.
  • Sending Board decks to all Board members at least 48 hours in advance of board meetings.

Involving the company’s leadership team with the Board and Staircase Ventures.

  • Inviting leadership team to present in Board meetings as appropriate.
  • Ensuring all CEO’s direct reports meet one-on-one with Staircase Ventures (or other Board member) at least semi-annually.
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The Importance of Shared Expectations and Staircase Ventures’ “Terms of Engagement”

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