Maintaining Bold

Written by Bob Harris, CAE

BOLD is a word frequently used in news headlines. “We need a bold plan to address guns in schools,” and, “Candidate unveils bold initiatives to curb violence.”

Bold can be described as an action or decision that demonstrates an ability to take risks with confidence and courage.


Seldom does bold describe the outcomes of board meetings and strategic plans. Directors tend to stay in comfort zones. Long-term thinking and taking risks by volunteers can be uncomfortable.

Bold can be described as an action or decision that demonstrates an ability to take risks with confidence and courage.

Examples would be a state association creating and copyrighting a course that is licensed to 49 state counterparts, generating new income. Or, a board creates a tech-based calculator that figures the direct and indirect return on investment of its members to their own communities.

Another example, an association that repurposes its foundation with a broader mission that draws new collaborative partners for significant community good. And an association that creates a for-profit service company that grows larger than the association itself.

Bold Strategic Planning

Most associations desire bold outcomes when strategic planning. A retreat is different from a board meeting.

A board meeting is designed to conduct business and make decisions, framed by an agenda and limited time. The planning retreat is scheduled to explore ideas, solve problems and to create a multi-year roadmap.

At the start of the retreat the chief elected officer implores, “This is our opportunity to create a strategic plan with impact; please take a bold approach today.”

At our retreat the chair repeatedly suggested a bolder approach to planning so that we’d be positioning the association for the next decade,” said Juva S Barber, Executive Vice President of the Building Industry Association of Greater Louisville.

Here’s the Problem.

Although the board was asked to be visionary and bold, directors fall into comfort zones.

It is not unusual for the board chair to repeat, “We seem to be talking about the things we already do, can we be bolder?”

It is easy to rehash familiar activities, tweaking them rather than creating dynamic new programs. Volunteers may only be considering activities for the short term. It can be difficult for directors to think beyond their terms and into the next decade, but that’s what is needed for a successful strategic planning retreat.

Bolder Outcomes

Techniques to support bolder outcomes at the planning retreat:

Focus on the Future – Prepare the strategic planning group by impressing, “This is the time to be bold.” Discussions about the good old days are wasted time.

Strategic Thinkers – Not all board members are strategic or bold. Tap the most strategic thinkers and visionaries for the retreat.

Too Many, Too Few – The right size for meaningful discussions is usually between 12 and 16 persons. Too many people and the day draws long, consensus is slower. Too few people and there may be less energy and ideas.

Balance – Retreat attendance should be balanced. Too many past presidents and not enough future leaders will skew results. Include the senior staff but don’t let them overpower the volunteers.

Limit the Time – An agenda that provides more hours than needed for discussion tends to get into the weeds. Just 5 to 7 hours can be efficient and effective.

Environment – I’ve done strategic plans in dark basements and the results were dismal. Be sure the environment stimulates big ideas. Use a location that is well-lit by natural light and promotes creativity.

Room Set-Up – An open-U is conducive to discussions where everyone can be heard without raising their voices or using microphones. Reading body language is important, thus being able to see everybody improves understanding. Set extra tables to break into groups for developing ideas and solutions.

Too Low – Everybody at the planning meeting should be cognizant of conversations that take the group into the weeds. Empower the group to regularly ask, “Are we thinking bold enough on this idea?”

Anxiety and the Agenda – Share a well-crafted agenda at the start. Too many retreats include games, trust falls and group hugs, creating anxiety for some people. Explain the agenda, time considerations, and try to adjourn early.

Creativity – Within reason creativity is encouraged. Just one good idea can transform into a windfall for the association when creativity is applied. Be conscious about limited resources (funds, staff and time.) Most retreats reference SMART goals: Specific, Measurable, Attainable, Relevant and Timely.

Facilitate – Someone should facilitate the retreat, responsible for advancing the agenda, promoting consensus and completing tasks within the schedule. Sometimes it takes firmness to herd discussions.

In the end, the intent is to reach bold, avoiding the comfort zone or rehash of old programs. The board chair and others may have to frequently remind the board to maintain bold.

Note: Bob Harris, CAE, provides free governance tips and templates at