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Gary A. Bolles will not use the word performance. He uses effectiveness, and the distinction is not semantics. Effectiveness is the state where what the organisation believes your role is and what you believe your role is are the same thing. Everything companies call a performance problem is usually those two drifting apart with no process to notice.
Who is on this episode
Gary A. Bolles is the author of The Next Rules of Work, a Global Fellow of Transformation at Singularity University, and an educator whose courses have reached around two million learners. He runs the consulting firm Charette and writes a regular newsletter on LinkedIn and Substack. His father wrote What Color Is Your Parachute, which comes up later in the conversation in a way that reframes how two generations think about work.
What they covered
Gary's model of work is deliberately spare: human skills applied to tasks to solve problems, which creates value for a stakeholder. Lay those tasks on a landscape and you get the single most useful idea in the episode. In the bottom left sit repetitive, well defined tasks you can measure and compare. That is where efficiency belongs, and where the whole industrial tradition from Deming onwards earned its keep. In the top right sit problems nobody has solved before.
"Versus the person who has to come up with the next billion dollar product, there is no efficiency up here in the ideation realm, zero."
Gary A. Bolles
The mistake he says Silicon Valley makes constantly is applying efficiency across the whole landscape instead of only where it works. On the AI question he frames every company as a portfolio decision across three things: people, technology and assets. Walmart has chosen a very large people slice with 2.2 million employees. At the other end of the spectrum, and the one every VC dreams about, is a business he describes as two people selling GLP-1 drugs online with a fleet of AI agents and a reported 1.8 billion dollar run rate. Most companies have to decide where between those two they want to sit.
His warning on automation is worth a CFO's attention. Software is good at executing the way humans already thought the task should be done. It is much weaker at the problem solving, so automating first means you have hard coded whatever process you happened to have, including the bad parts. The way through is a lot of small experiments pushed down to team level, then propagating the ones that work.
Then performance reviews, which he calls a myth we tell ourselves: one magical process in which everyone agrees what the problems were at a point in time, never updates it, collects supposedly anonymous 360 feedback, synthesises all of it and arrives at a verdict, at scale. His alternative is synchrony, a continuously updated agreement between organisational goals, team goals and individual goals, plus what he calls synchronous rewards. The analogy there is cybersecurity: the industry abandoned perimeter strategy for a security of one, where access depends on who you are, what you are working on, where you are and what you are using. Rewards, he argues, should work the same way rather than being averaged across thousands of people.
Key insights
- Effectiveness is alignment, not output. If the manager's expectation and the worker's expectation of the role are in sync, you have it. Most performance management is an expensive way of discovering they are not.
- Efficiency belongs only to the repetitive end of the task landscape. In ideation it is actively wrong, because more ideas means more raw material to sift, not waste.
- Automate second. Software reproduces the process you already had, so look at the problem you are solving before you encode the steps you inherited.
- Personalise rewards the way cybersecurity personalised access. A standard menu plus a few options is the perimeter model, and Gary's point is that perimeter thinking is dead everywhere else.
- Young workers have inverted the ladder. The old sequence was get paid, then get good at it, then maybe enjoy it, then serve the world in retirement. Gary says the new sequence starts with what the world needs and works down to pay, which is why purpose questions baffle older CEOs.
- Engagement is the wrong frame. He uses degree of membership instead, borrowed from fuzzy set theory, because employment is no longer binary and neither is commitment. His number: two thirds of young people in surveys say the day they take a job is the day they start looking for the next one.
Watch the full conversation on YouTube, or listen to the audio version on Apple Podcasts.
