The summer finally hit Tokyo in the last week. From the clients, family, and friends in the states, I have heard some horror stories about the heat. If what I saw in Nikkei yesterday is any indication, then it’ll be just like Singapore for the next few months.

Over the last month, a few things have been keeping me busy. One is a recent post looking at using AI to generate a mock of an acquisition target’s apps to help figure out not just your gaps, but also which questions to ask once the deal closes. Another is a webinar I am putting together for those that are either about to close or just recently closed on their acquisition. Lastly, is a thought exercise based on a recent client discussion on what to do after everything has been migrated.

Starting with the blog post, the idea originated from a talk I recently attended by Bain highlighting some of the due diligence exercises they were working on for their PE clients. They were showcasing how to determine how much of an impact AI will have on a prospective acquisition target using SaaS as an example. What they didn’t mention, but I saw the next day in the FT was how they were relying on vibe coding a prospective target to evaluate the same criteria. This is what inspired an idea of “what if you had a way to evaluate the software you had to bring over?” The post can be read here.

In short, the idea is to attempt to mock up something your acquisition target would have (which you should have a rough idea on based on the initial due diligence). This would be something your tech teams could poke at to figure out what questions they should ask once the deal closes and it is time to get the integration planning underway. Thus, reducing the very expensive risk of the integration work grinding to a halt due to a missed assumption or forgotten dependency.

Speaking of the due-diligence, pre-integration planning sessions, one of the things I’m putting together for this quarter is a webinar looking at the approach I’ve taken to get a holistic look at the proverbial boulders and drilling down into what needs to be accounted for when fleshing out the integration plan. As this will be the first time I’ve put something like this together, this will be for free in exchange for feedback afterwards.

If you, or someone you know is a tech leader that has just closed on an acquisition, then this will be of most benefit for you. Reply to this newsletter, and let me know you’re interested and I will add you to the notification list.

Lastly, a recent client conversation prompted a thought about what happens to the tech debt that is accrued after finishing the initial integration? Think about the scripts and code to help migrate the apps and data over into your systems on a compressed timeline to make the TSA or reporting deadlines. How much of it is still in place, and at what point would you take time to remove it?

There is the risk of keeping something fragile in place where if you remove it, then the underlying systems could break bringing your business down with it. Yet if you keep it in place, then it would add additional risk of failure by requiring additional support and maintenance to keep everything operational making it much more expensive to maintain in the long term.

Which way would you go?

Until next time!

Chris (cab)