Questions clients ask me #3

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How Do I Make the Transition from Senior to Executive Leadership?

When coaching clients I am often asked the question: what do I need to know to make the transition from being an already experienced leader to being effective as an executive leader?

It’s an interesting, and sometimes surprising, question given that they will already have years of experience as leaders. I believe the reason they are asking is because of the realization that the most senior executive roles are often differentiated from other leadership roles by the:

  • Weight of ultimate accountability
  • Complexity and breadth of oversight responsibilities
  • Challenge of motivating others to accept accountability for problem solving
  • Difficulty of learning to ask questions rather than give answers
  • Degree to which messaging has to be effective at a distance

This is not to say these factors don’t play a role to some degree at all levels of leadership, but at the most senior levels each of these generally carries greater consequences for the organization. So, let’s dig in and look at what I’ve often found helps leaders I work with successfully make this transition.

The weight of ultimate accountability

With progress up the leadership hierarchy the spike you sit on gets sharper. The company depends on you to make good decisions and provide clear direction. If you screw up, given you operate in a more rarified space, there are less places to hide. The biggest challenges in business are almost always cross-functional in nature, so it is worth taking note of the old proverb ‘a problem shared, is a problem halved’. Working together as a team with shared purpose rather than as a set of individuals makes obvious sense. And yet, based on my own experience, I would say that the majority of senior leadership teams do a lot better at building impervious boundaries around their individual roles than seeking the collaboration of their peers. Occasionally I do wonder what the point of regular leadership meetings are when they become a series of individual statements rather than real discussions!

Effective executive leaders: see peer leaders as their team, not a collection of individuals. They invite collaborative problem solving, focus on the interdependencies inherent in complex problems, and strengthen peer relationships through building a sense of shared accountability.

The complexity and breadth of oversight responsibilities

At the most senior levels the nature of the complexity and demands of oversight tend to be less narrowly technical, and more a result of the interplay of multiple variables across diverse problem sets for which there is no right or wrong answer. This usually means a high degree of dependence on the work of others and, given their time is usually extremely limited, close involvement in the details is often not possible.

It probably doesn’t get much more complex and consequential than being in the White House Situation Room. In his fascinating book The World As It Is, Ben Rhodes describes a great example of President Obama showing leadership under complex and challenging circumstances: he listened to the views of all his leaders, summarized what he had heard, provided perspective, stated what he required and by when, and then left them to get on with the work. He resisted the temptation to get stuck into that one situation, knowing he had plenty of other demands on his time.

Effective executive leaders: Listen carefully, ask good questions, give clear direction, specify expected outcomes and timeline, and then delegate responsibilities.

The challenge of motivating others to accept accountability for problem solving

Generally speaking, early career progress is built on solving narrow technical problems, engaging well with teams who are closely connected, tapping into one’s own experience and showing your strengths, all while making as few mistakes as possible. As we have already noted, senior leadership levels deal with broad problems, teams with diverse skills and locations, and have to resolve issues for which they are not necessarily expert and, therefore, need to draw on their team.

In an excellent podcast (#194 of Finding Mastery, Pete Carroll, acclaimed head coach of the NFL Seattle SeaHawks, describes his approach to coaching as being able to make people feel capable and motivated and to feel trust in him and themselves. In other words he suppresses his own ego-driven desire to solve the problem himself and tell them what to do; instead he focuses on building their self-confidence and motivation, knowing that will help them to perform at their best and feel enabled to make decisions on the football field.

This doesn’t mean he avoids tough decisions: players get side-lined or dropped all the time. What it means is that, however things turn out, they believe they were supported and that their relationship with the coach had integrity. This idea of the player-coach model of leadership is talked about a lot in business literature, but Coach Carroll showed the power of linking intention to action. In sport as well as in business, done well, I have seen this manifest itself in people who are really motivated to give their best and excited by the challenges before them.

Effective executive leaders: focus on building confidence and problem solving skills in each of their team members

The difficulty of learning to ask questions rather than give answers

Unfortunately, subordinates have too often been conditioned to expect leaders to do the problem solving and tell them what to do. At the same time, old habits die hard and frequently leaders jump into problem solving mode as soon as they see staff stand back and await direction. The result is that team members have under-developed confidence, logical thinking and problem solving skills. So, even if motivated they may struggle to arrive at a satisfactory conclusion (interestingly the 2018 WEF Future of Jobs report has critical thinking and analysis 5th and reasoning, problem solving and ideation 10th on it’s list of skills growing in importance for 2022).

Jonathan Neman CEO of Sweetgreen in discussion with Guy Raz of How I Built This fame, described how he sees his role as CEO: setting strategy and direction and ensuring the necessary resources are available. That is, establishing the conditions necessary to enable other people to do their job.

As executive leaders that’s one part of the equation. The other is to improve ones own skills at asking good questions that lead team members to arrive at answers for themselves and at the same time learn the power of logical thinking and problem solving.

Effective executive leaders: Provide the conditions for success, strengthen their team’s capabilities by asking great questions instead of giving answers, using those questions to show how to break down a problem, and develop courses of action. They support and enable, rather than do.

The degree to which messaging has to be effective at a physical and hierarchical distance

We all know the game of telephone and have seen how easily messages get increasingly distorted the further they are from the initiator. With team members who are not physically close to a leader, it can be hard to provide clear messaging, motivate members, and ensure they are engaged. There are 2 challenges here: Medium and message.


There are some amusing YouTube videos (e.g. this one) showcasing the horrors of relying on conference calls to be effective replacements for physical meetings. As they so clearly point out, the challenge is both technological (quality of signal) and human (inattention). The first is one for IT to solve, but the most effective method to overcome the second is the use of video conferencing (assuming an in-room meeting is not possible).

Just as being in a room together improves the focus and attention of participants, so does knowing one is visible to other participants, even when virtual. Some companies have recognized this and established video conference as the norm for calls (e.g. Facebook), but it amazes me how few have done this, despite what must be the possibility of potentially huge productivity gains.


Clear messaging and meeting management is the other requirement, all too often made worse by inadequate thought being given what needs to be said and poor skills in checking for understanding. A few simple steps can make all the difference in making meetings (virtual or in-person) more effective:

  • Pre-meeting – know what you want to say and the outcome you are looking for
  • During meeting – set a clear agenda, ask questions to ensure understanding
  • Post-meeting – ask for feedback, ask yourself what you could have done better

Effective executive leaders: increase participant attention through the use of the right technology, manage their messaging effectively, and ask good questions to test for understanding.

The transition to the most senior ranks of leadership is demanding and experienced differently by each individual. If you are looking for coaching support, let’s chat. Redwood Advisory Partners coaches executives to help them perform at their very best under new or challenging circumstances. 

Follow or connect with Stephen on LinkedIn or visit our website at You can contact Stephen direct by email at [email protected]

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