July 2, 2026
How To Move From Execution To Advisory
On today’s Ditcherville LIVE session, I was asked:
Is your suggested method for transitioning from execution to advisory as a software developer still to suggest a paid roadmap as a precursor to execution? Any other ways to approach it?
Yep, roadmapping is the main way.
With new clients, make them “come in through the strategy door” as David C. Baker advises in The Business of Expertise.
What does that look like?
I’ll use a software project as an example...
Usually, when you have a software project that comes in, the first short period is where you do the high-level, big decision stuff that you’re probably only going to decide once.
- Maybe it’s deciding on the stack
- Maybe it’s picking models
- Maybe it’s an architecture diagram
- Maybe it’s a security assessment
Whatever you normally do first, the move is to carve off that piece at the beginning and sell it as an independent roadmap, blueprint, architecture, or assessment.
Fixed price.
Fixed scope.
At the end, they’ll have clarity about what to do, when to do it, and in what order.
They can take the roadmap to someone else, or they can ask you to give them a quote for the build phase.
That said, I mentioned a couple of other ways to try to transition to advisory...
Paid Calls
The easiest possible advisory engagement to set up is a paid phone call.
Just connect your Calendly to Stripe, and you’re ready to sell.
What does the client get?
By the end of the call, they’re going to have some clarity around whatever the big business question is.
This is valuable to people in urgent, high-stakes situations who really want to talk to an expert to map out the unknowns.
How easy or hard this is to sell depends heavily on how well-known you are as an expert in the space.
Executive Meetings
Another way to start to transition to advisory is to watch for situations where existing clients are pulling you into meetings with senior leaders about something different from your existing project with them.
It might be a different type of project, or a sub-specialization within your expertise.
On the call, I described it this way:
If you’re getting pulled into meetings in an advisory capacity, then that is a signal that you are positioned in their minds as trustworthy about this thing.
If you see signals like this, you could potentially:
- Try to spin up a secondary engagement inside of this company to advise them on this other project
- Create this sort of advisory engagement as a productized service on your website, and sell it to other clients
Both are hard to do, but probably worthwhile if you’re getting organic signals that your client trusts you to advise them on whatever the thing is.
Common Failure Mode
One warning:
If you really want to move into advisory work, execution positioning can undercut you.
If your website says you do the strategic thing AND the tactical thing, it is harder to present yourself credibly at a strategic level.
Even if you still do the tactical stuff, I wouldn’t talk about it in my marketing.
A new client has to do the strategy thing first, and if you want to do the execution for them after, you can tell them directly that that’s an option.
Hope that helps!
BTW - This is the kind of question that comes up every two weeks in Ditcherville LIVE, my group Q&A session for independent consultants who are done trading time for money.
If you’ve got questions like this rattling around in your head, come get them answered:
Hope to see you inside!
Yours,
—J