Do your tech advisors – everyone involved in delivering a technical solution, including developers, data scientists, product managers, testers, and the like – grasp the needs of your organization or one you might consider acquiring or investing in? Where is your tech strategy strong? Where does it need improvement? Is your investment in salaries and equipment paying off, or is your money disappearing into a bottomless pit?
If you are a non-technical executive who needs technological solutions and innovations to achieve your goals, it can be incredibly frustrating to negotiate with the technical experts who hold the keys to engineering success. When veteran tech leader and coach Douglas Squirrel was asked how to have confident, profitable conversations with your engineering team, he had some profound insights.
Start by Asking Lots of Questions
And insist on business-meaningful answers, not technobabble. Build up your understanding bit by bit: ask what the engineers observe, why they select those items to pay attention to, what it means to them, what conclusions they draw, and only then what actions they’re taking. Once you have a jointly-held, non-techie understanding of the situation, have the engineers be accountable to you for their actions, using the language you agreed on — showing you real, live results as frequently as possible. (I teach tech teams to release new, valuable software every single day. How fast is your team?)
Improve the Profitability of Your IT Investment
If you have organization and market fit but no execution, you disappoint customers. If you have execution and organization but no market, you have no profits. And if you have market fit and execution without organization, you’re a ship without a rudder. Only with all three is your tech team set up for success.
To read the pluses and minuses of an engineering organization right away, check for those three elements! The details are in my Tech Radar booklet, but briefly, you can verify organizational maturity by checking seniority and trust, execution by looking at testing and monitoring, and market fit by examining the frequency of customer feedback and their willingness to pay.
Agile Development, Lean Software, or DevOps: Why They Just Don’t Work
Viewing people as mechanical, interchangeable parts and expecting them to act as such ignores human nature and is doomed to failure. Organizations have embraced the process and tools created by the agile transformation, yet the “new” methods merely replaced the old-school factory mindset with a cubicle model.
The first thing you need to do to focus improvement efforts on harnessing the unique attributes of people is to junk the Gantt charts and stop shipping projects to Remoteistan as if the teams doing the work were completely fungible. Bring tech people into business strategy discussions early and ask them genuine questions about whether what you’re doing makes technical and business sense. By jointly designing what outcomes you want from engineers, you’ll get much more commitment from them and better results, too. Look at the difference between Boeing, which suffocated from traditional, rigid project management and was unable to get Starliner back home, and SpaceX, which blew up spaceships right and left and valued learning over being “right.”
The Tyranny of Structurelessness
Most organizations I work with have no idea how to answer the question: What do you do to generate ideas for your tech team? They mumble something about talking to users and tracking suggestions in Jira but have no defined method for turning those inputs into anything like a strategy or even a task list. So, how does one communicate ideas and make sure they keep flowing?
Start by defining your negative space — the features and ideas and customers you won’t pursue, that you’re ruling out of bounds. Once you stop trying to be a one-stop shop for every clever-sounding idea, there will be much more room for creative, quieter voices to be heard. And you’re really set if you have a solid mechanism for rapid feedback on what you’re doing — customers should be surprising you with new learning every single day!
Platitudinous and Tech Recruiting
When you are scouring for outstanding tech executives, you want to look beyond the typical resume that says what they did – but not why. You want to look for the rare job-seekers who actually describe their business impact. This is extremely important.
Too many people at all levels of our organizations are trapped in doing and not thinking. Their activities, like reporting or testing or answering customer queries, are incorrectly taking precedence over their outcomes, like faster releases or better data or better-informed customers — and just executing the same strategy your competitors are following is no road to success. So, what should we be looking for? Executives who shift gears rather than just pressing harder on the accelerator are rare and highly valuable. To pick them out from the haystack, ask them to tell you stories about disappointing others helpfully and shaking teams out of complacent compliance.
The 90-Minute Tech Radar Assessment

Do your tech advisors and everyone involved in delivering a technical solution grasp the needs of your organization or one you might consider acquiring or investing in? Where is your tech strategy strong? Where does it need improvement? Is your investment in salaries and equipment paying off, or is your money disappearing into a bottomless pit?
Anyone, no matter how non-technical, can spend about two hours answering the questions in the Tech Radar assessment chart in Squirrel’s Tech Radar and walk away with a clear sense of the profitability and effectiveness of their IT team. There are six key axes along which to check the team. Some of these you can see directly, and some require digging in with engineers, but all are easily accessible and quickly verified and scored. You wind up with a chart like the one below, showing strengths, weaknesses, and what your tech team needs to grow and deliver rapid value.
				