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Simon Says: Why some leaders stay operational instead of being strategic

Gif courtesy of Tenor

This post is a reflection on a recent conversation I had with a local government client. Although the situation involved one municipality, the themes are far from unique. In fact, they’re global – spanning organisations and industry. They simply become more visible in politics, where expectations are high, scrutiny is constant, and the work is deeply personal.

My client was concerned about the dynamic emerging between councillors and staff. On one hand, the new councillor group was incredibly enthusiastic and genuinely motivated to make meaningful change. On the other, they were getting pulled into operational detail and struggling to create space for strategic thinking.

This created two challenges:

  1. The leadership team was spending significant time reviewing low-level operational decisions.
  2. Councillors weren’t able to dedicate the time or headspace needed for the bigger strategic questions councils must grapple with*.

*These include issues like fiscal sustainability, AI integration, climate preparedness, social cohesion, and balancing housing growth with environmental protection.

Their questions to me were simple: “Why are they operating this way?” and “Is there anything we can do to help?”

There is a well-known adage in business known as the Peter Principle. Named after its author, Laurence Peter, the adage states: “In a hierarchy, every employee tends to rise to his level of incompetence.”. 

The premise being that if people are good at their job, they’ll be promoted – and they’ll only stop being promoted once they’re not very good at it. It’s one of those sayings that makes us laugh because we recognise the truth in it.

But apart from being an interesting paradox, there’s more to the Peter Principle than first meets the eye. It’s not just that higher roles in the hierarchy demand greater skill – it’s that they require a different set of skills.

Entry-level roles tend to be technical and task-based, but as people move up, supervising, managing, and planning skills become essential. By the time you reach the top – CEO or board level – the role is fundamentally about strategy, oversight, and relationship-based decision making.

So according to the Peter Principle, if you have preference for technical work, and you’re good at it, you will most likely get promoted out of the lower levels of the hierarchy. Which means that over time you spend less and less time doing the work you’re good at and love –  and more and more time doing work that’s outside your wheelhouse*. Work where you ultimately feel less capable and less confident.

* This is often reinforced by the promotion and reward systems used by organisations, which tend to do a much better job of measuring technical performance over social performance.

Figure 1: The Peter Principle as a career trajectory. As an individual moves up the hierarchy, roles shift from being technical and operational to strategic. As people are promoted, they are also given access to more training, which allows their capability to increase. As soon as an individual’s capability doesn’t meet the requirements for the next role in the hierarchy, they will no longer be promoted – and will experience a gap between confidence and competence.

The Peter Principle highlights that as people progress, they’re often asked to step into roles that require a very different set of skills to the ones they’ve mastered. This can be confronting to an individual’s sense of identity and control. Research suggests that in such situations, it’s unsurprising that some people will choose to reassert their capability and confidence in other ways.

One way this often manifests in business is through micro-managing.

Micro-managing is easy to label as a trust issue, but more often it’s a confidence issue. If someone has deep technical strength but feels less sure in their leadership role, it makes sense they’d lean back on what they know.

From the outside it can look like control. On the inside, it can feel like competence.

And like the councillors in the earlier story, when leaders focus heavily on detail, it’s often because they care deeply and want to do the right thing—they just don’t yet feel equipped for the strategic work they’ve been asked to do.

The situation above won’t be news to some of you. Most organisations understand that role requirements change as people are promoted, so they offer ongoing training and development as staff move up the hierarchy*. In corporations, this transition might happen over years, or more likely, decades.

*I would argue this is a good solution, but not necessarily a great one. It acknowledges the different skill sets required for leaders and seeks to close the gap. At the same time, you’re still constantly taking incredibly competent technical people out of the roles they excel in and asking them to do something else. Research has shown this tends to have a negative impact both on the performance of the leader and the performance of the staff they are leading.

On the other hand, people elected to council are expected to make this transition very, very quickly. Councillors don’t have years of learning and development to prepare them. Instead, they get a six week induction program, after which they’re expected to immediately start work on a four-year council plan with a $100m+ annual budget. Councillors are thrown in the proverbial deep end and expected to either sink or swim.

It’s unsurprising that if someone lacks confidence and you throw them into the deep end of the pool, they will head for the shallows. Being able to touch your toes on the bottom gives a sense of safety and control.

During the conversation I had with my client, this was one of the themes that emerged. They shared the story of one particular councillor who was a retired engineer. This councillor had become particularly focused on some of the engineering decisions related to an upcoming project. While this might have been framed as oversight, I have no doubt it would have felt reassuring for that councillor to swim in some waters that felt safe – knowing they could touch the bottom of the pool.

The truth is, we all have a tendency to spend time in familiar waters. We focus on tasks that feel manageable or rewarding, even if they don’t always have the highest strategic impact. My friend Dr Jason Fox calls this the delusion of progress. Checking emails, attending meetings, reading reports, or writing articles (possibly even ones like this!) can incrementally build confidence to head for deeper water and undertake deeper work, much of it is just a distraction.

It’s worth stressing that the deep end of the pool councillors are thrown into is deeper than most. Councillors regularly make decisions that impact 100,000 or more people, cost tens of millions of dollars, and have intergenerational consequences. Not only are these significant decisions, but they are expected to be made in collaboration with a group of diversely opinionated peers and under constant public scrutiny.

I point this out because most of the people who grumble about local government will never face decisions like this in their lifetime. The capabilities and knowledge required to be an effective councillor are quite unique. You need to understand the diverse responsibilities of local government, have sound financial skills, group decision-making acumen, negotiation abilities, strong interpersonal skills, knowledge of land-use planning principles, and the capacity for strategic thinking.

Many councillors are extraordinary community members – scientists, small business owners, teachers, public servants – who bring passion, commitment, and a wide range of experience. But they aren’t necessarily experts in governance, finance, planning, or strategic decision-making. 

And they’re not meant to be.

The real qualification for being a councillor is caring enough about your community to carry the weight of competing needs while being publicly held to account.

That’s a courageous act in itself.

You can find my extended musings on the idea of replacing councillors with a board of directors here.

Figure 2: The Peter Principle as it applies to Councillors. The strategic skill requirements for a councillor are significantly higher than most commercial roles. In addition, these skills would be developed over years or decades in most organisations, yet councillors require them immediately. This can lead to a significant competence and confidence gap.

It’s disappointing but also unsurprising that training is more often than not seen as a cost rather than a source of value. The way organisations budget and put money in different buckets means the cost is often incurred in one part of the organisation (learning and development), while the benefit accrues elsewhere.

What this means is we don’t always invest money in the right training. It also means we sometimes look at training through the lens of ‘what’s the minimum level required’ rather than ‘what would have the biggest impact’.

But if local councils were to align training budgets with value creation, I would strongly argue the Return on Investment (ROI) for supporting councillors in strategic thinking and collective decision-making is an order of magnitude better than any other training you can think of*. I appreciate this is a bold claim, so here is my rationale.

*The only exception I can think of is certain types of occupational health and safety training that have life or death implications. Though you might be able to think of other examples.

  1. Councillors are responsible for all the biggest financial decisions within the council (in my municipality, this means any contract over $1.1m)
  2. Councillors are responsible for all the biggest strategic decisions within the council. I know one regional council where councillors are currently debating whether to build a new $30m library. Beyond the financial impact, this is a project that will have intergenerational impact.
  3. Councillors aren’t engaged on a skills basis. This means there is often a notable proficiency gap, and significant improvements could be achieved if the right support is provided.
  4. The cost of doing nothing is also substantial. As noted by my client, an operationally focused councillor group consumes significant time and resources.

In fact, the potential ROI of councillor training is so high that it’s ludicrous to stick just to the mandatory training guidelines. Although there is some value in establishing a compliance-based floor, I would argue there is significantly more value in raising the performance ceiling.

I genuinely believe that investing in a councillor group to become more proficient strategic thinkers and decision-makers should be a no-brainer. The biggest challenge, however, is the time required to build those skills. In private enterprise, developing this level of capability might take decades before people are considered “ready.” Councillors, by contrast, have just a four-year term and are often juggling the role alongside other commitments, putting in significant additional hours. Expecting them to invest even more of their own time in training isn’t always realistic, regardless of who covers the cost, and traditional training models rarely fit the immediacy of their workload or the pressures of the role.

If we acknowledge that strategic thinking and decision-making skills are valuable, but also recognise that councillors don’t have the time to invest in extensive training, what’s the solution? The answer is: we do what we can.

As another local government leader pointed out to me, we already have a model for this. We don’t expect our councillors to be experts in all aspects of the law, so they keep suitably qualified lawyers on retainer, ensuring they are available when (not if) needed. Strategic thinking and decision-making can be approached in the same way. Rather than expecting councillors to be immediately proficient, we ensure they have access to a coach who can support them when (not if) required.

Many executives use external coaches for the same reason, and councillors can benefit even more. With a coach:

  1. Councillors don’t have to wait years to develop proficiency—they can access guidance and capability immediately.
  2. Learning can be incremental, delivered in short sessions, over coffee, or by phone as needed.
  3. Coaching is tailored to real-world challenges, unlike formal training, which can be generic.
  4. Councillors develop skills that are valuable both within council and in other parts of their work or life.
  5. Most importantly, a coach provides independent support and advice—not directives—enhancing the integrity of the decision-making process.

In short, coaching is a practical, flexible way to help councillors gain confidence, strengthen strategic thinking, and make better decisions, without the pressure of having to master everything immediately.

I’ve been working on this post for so long it’s sometimes hard to know where to end. Good blogging practice would tell me to end with a ‘call to action’, but perhaps a ‘call to reflection’ is more appropriate.

  • Does the challenge identified at the beginning of this post resonate with you? Do you have leaders (either inside or outside local government) that are spending more time on operational tasks than they should?
  • If so, is this a trust problem whereby they don’t trust others to do their job properly, or is it potentially a case of compensatory control?
  • What are the important skills gaps that your leaders might be facing, and what is the value of helping close them (in the case of decision-making, I often talk about “what’s the value of one good decision”)?
  • How does coaching stack up against other training options in terms of time, cost, and efficacy?


Simon

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