Almost nobody arrives at this on a plan. It is triggered, and the trigger usually has a date on it that somebody else set.
The question companies ask is whether they are big enough yet. It is the wrong axis. Size correlates loosely with needing technology leadership and predicts almost nothing about when, because the thing that creates the need is not headcount. It is a decision arriving that the current arrangement cannot make well.
A sixty-person company midway through an acquisition needs this more than a comfortable three-hundred-person one that is not deciding anything. The first has four directories, two contract sets and a date; the second has a working estate and a quiet year. Headcount says the opposite in both cases.
The more useful test has two parts. Is there a decision coming whose consequences outlast the people making it, and is there somebody accountable for getting it right whose job is not something else. Where the answer is yes and no, in that order, the timing is now, whatever the headcount says.
This is also why it is almost never planned. Nobody budgets for technology leadership in the abstract. They ring somebody in the week after the incident, the resignation or the diligence request, which is later than ideal and still the right call.
The signals accumulate quietly and none of them is individually urgent, so the decision waits for something loud. By the time it arrives, the deadline belongs to somebody else and the available answers have narrowed to one.
The signals below are all observable and all checkable this week. Acting while there are still several answers available is the whole of the difference, and it costs less than acting when there is one.
Observable things rather than feelings. Every one of these is checkable in an afternoon, which is the point: a signal you cannot verify is an anxiety.
The questions arrive before the capability to answer them does.
Money is moving on decisions nobody owns.
The exposures are known to somebody and written nowhere.
The knowledge is in a person rather than in the company.
Consequences rather than percentages. Every one of these is something a reader can check against their own last two years.
This is the part people miss. Waiting does not defer the decision, it delegates it, usually to whoever raised the topic or whoever is selling something. A default is still a choice, it is just one nobody reviewed.
Early in a renewal cycle you can negotiate, run a selection or walk. Six weeks out you can renew. The set of available answers shrinks on a schedule that has nothing to do with when you get round to it.
Unused licences, overlapping tools and an overrunning project do not appear as a line item called waste. They appear as a slightly higher number every year, which is exactly the shape that never triggers a review.
Every month of undocumented change makes the eventual audit, diligence or insurance application longer and more expensive, and those deadlines are set by other people.
Each of these has its own page: what is actually going on underneath it, what to do in what order, and what you should end up holding.
Size is the weakest predictor of the four. The band where this usually fits is roughly 50 to 500 people, or $10m to $250m in revenue, but the useful question is not headcount. It is whether a decision is coming that the current arrangement cannot make well. A 60-person company midway through an acquisition needs this more than a comfortable 300-person one does.
No, and this is the most common way these engagements start. Almost nobody hires ahead of the trigger; they hire in the week after the incident, the resignation or the diligence request. Later is more expensive because options have closed, but the work is the same work and the first ninety days do not change.
Usually the opposite. An in-flight project is one of the clearer cases for bringing somebody in, because a project that is drifting rarely corrects itself and the cost of that drift is being paid weekly. Waiting until it finishes means paying the full price of whatever went wrong and then reviewing it.
Then it is worth a conversation rather than a proposal. Whether the timing is right is exactly the sort of thing an intro call settles quickly, and a firm that cannot tell you honestly that it is too early is telling you something about how they sell.
That is a thirty-minute conversation rather than a proposal. If the answer is not yet, we will say so.
