ThemeStrategy & Direction
CardCard 9 of 66
Questions5 to explore

Challenges

Hurdles you see or imagine ahead

The challenges an organization knows about but has not written down are the ones most likely to surface at the worst time.

Every organization is navigating a set of pressures it can see coming: a market shift, a technology change, a funding gap, a dependency that creates risk. Capturing those challenges does not solve them, but it does ensure they are visible to more than one person and that conversations about them can happen before they become crises.

Challenges that live in a founder's or executive's head have a way of generating anxiety without generating action. Writing them down shifts the relationship with them: they become things to track, plan around, and involve others in addressing.

The goal is not a formal risk register. It is a working list that is honest about what is difficult, who is watching each challenge, and what the plan is, even if the plan is incomplete.

What to capture

For this part of the company brain, what is worth writing down and keeping current. The goal is not a complete archive but a living record that new people can read and returning people can trust.

Known challenges & owners

A plain list of the pressures and obstacles the organization knows it is facing, with at least one person named as responsible for watching each one.

Timeline & urgency

A rough sense of when each challenge is likely to matter most, so priorities can be set and the list does not feel equally urgent all at once.

Current responses

What is already being done, or considered, for each challenge, including partial or exploratory responses, so progress does not disappear when the person working on it is away.

Questions to explore

Use these on your own or in a group. There are no right answers, only better conversations.

What are the two or three challenges that keep the most senior people in the organization up at night?
Which challenges are known to leadership but not visible to the broader team, and is that the right choice?
Which challenges are external and which are internal, and are both types being tracked?
Who owns each challenge, and what does that ownership actually mean in practice?
When did the organization last review its challenge list, and how much has changed since then?

Things to notice

Challenges that feel too sensitive to write down are usually the most important ones to document, even if access is restricted.
Challenge lists often grow without shrinking; when challenges are resolved or become irrelevant, the record should reflect that.
Conflating challenges with risks can make both lists less useful; a challenge is something being navigated, while a risk is something being managed against.