Thoughts on Leadership Transitions

8 min readOct 13, 2019

Recently, I shared some reflections I had on my first 6 months in a new job. The reaction on Twitter was very kind and supportive, so I thought I’d consolidate and augment my thoughts with the aim that they are more generally applicable. I’ve split it into two parts:

  • lessons for you as a leader when you’re transitioning into a new org
  • tips for teams who are receiving a new leader from outside the org

Please remember this is based on my personal experience not an extensive study! I’d be interested to hear how generic these lessons are or if I’ve missed a blindingly obvious one.

Contrast of my travel transition. Leeds and Kettering train stations

Lessons when you’re transitioning in

  1. Do some structured preparation. Don’t just rock up and think you can wing it, particularly if you’re taking a big step up or into a new sector. I used The First 90 days by Watkins. It is an superb, thought provoking and practical book, but I’m sure other equally useful books are available. What ever book/blog you choose, don’t just read it, properly engage with the exercises in each chapter. Make a list of things that you’ll come back to a few weeks or months later and actually follow up on it.
  2. Start with realistic expectations. As much as you feel like it, don’t be tempted to leap into action on all fronts immediately. Your first impressions may not be accurate. Equally, recognise when you feel that there is so much to take in, you can’t work out what fire to put out first. In that circumstance, you need to realise that those fires aren’t new, and they were burning before you arrive. Pick just one for now and work on that. The other thing is get some help, either internally or externally. My new boss described that as “sorting out your iron lung”.
  3. Don’t expect your structured preparation to be enough. It’s good to read everything you can, talk to people in the know to prepare yourself for joining, but be adaptable and be prepared to take on new learning. I read loads of books, went to talk to other people in similar roles, met all my peers before I started, wrote a 90 day plan, bought some new shirts and arrived on day 1 the most prepared I’ve ever been for a job. However, nothing fully prepares you for the specific business orientation, stakeholder connections, expectations and cultural norms of the organisation, even if you’ve come from a similar sector. Six months into my new job, I’ve looked back at the list of transition traps Watkins says leaders fall into and I reckon I fell into at least three of the six mentioned, and this was with my eyes very much open, so don’t beat yourself up, this stuff is hard.
  4. The feedback you get in the early days may not be actionable. The First 90 Days recommends you get some informal 360 feedback after the first 30 days. My impression was that people didn’t know me enough by then to have formed any meaningful opinion. They did however suggest things that would help in my orientation or what they wanted to know about me and my planned approach which was helpful, but not what I’d class as feedback. I’ve found that the feedback I’ve got later on has been more actionable, but I guess it depends on your situation and your peers.
  5. Establish your ‘how to get stuff done’ framework. There are a number of practical things that can trip you up if you don’t know them, and you don’t consciously know that you don’t know them at the start, but without them you’re hampered. Some of them *ought* to be kind of obvious, but I missed a few in my transition. Here’s the list I wrote for my future self:
  • What are the steps for a procurement? What approval steps are there? Who can raise a requisition? Are people familiar with the frameworks you need? Is there a stock template that references the requirements for strategy alignment for inclusion in invitations to tender?
  • What’s the method for securing funding over and above budget? Who chairs that group/committee? Clarify if revenue and capital are managed by the same finance partner.
  • What’s the steps for recruiting staff, agency or contractors. What approval steps are there? Who has responsibility for which parts?
  • For large offices/locations, do you know your way around, and the difference between what the signs say and what people actually call it. Later than ideal, I marked up the standard site map with other names I’d heard. That way, you do stand a chance of arriving at that meeting in the right spot.

6. Don’t be pushed into declaring your strategy too early. Similar to the temptation to push for action, people will ask your opinion on things and your future view very early on. I had some ideas, but just painted some big picture stuff rather than being pushed to set out the detail. I was glad of this, because much changed once I’d understood more.

7. Do something daft (but safe) that reveals your personality. A few weeks into the new job I went into a meeting and realised that I was wearing the same shirt as one of my peers. Unforgivable. So the WhatsApp group ShirtAlert was born. Every morning I take a photo of my shirt and share it with my colleagues to avoid those sartorial clashes. It created some light hearted banter early on, created some social cohesion and we are still using it 6 months later.

8. Shut up about your last job. The important final point. This isn’t your last job, this is a new one. What you did there may not apply in the new gig, and even if it did, people don’t want to feel like you’re just going to do a cookie cutter replication without understanding their particular pain points and ambitions, so keep references to “when I was at x” to a sensible minimum, to avoid the justified eye-rolling.

ShirtAlert WhatsApp group

Tips for receiving a new Leader

Here’s some thoughts on how you might be able to prepare for someone new coming into your organisation. This is based on my experience of receiving new leaders in the past and my observations about what I liked (or would have liked) from teams in my previous transitions.

  1. Do some structured preparation. Don’t assume that your years of corporate knowledge is easily assimilated or articulated. Write some stuff down that explains what your team/area does in a simple form. Don’t wait to be asked. Set out the current workplan, team structures, budget position, challenges and opportunities. Make sure you highlight what things you’re proud of over the past few months — if you can’t do that easily, then that’s a hint to start making a future habit of writing this stuff down, because you will have done loads of brilliant things that you should be rightly proud of. Also, don’t assume that those good things will be obvious. In my experience, once you’ve got that sort of documentation together, it comes in very useful in many circumstances, so even if you’re not bothered about making a good first impression (and you should) it is an investment worth doing anyway. If you can send that over before the new leader starts, then all the better, as once they land, their head will be spinning too much in those first few weeks to properly take it in. If you’re really keen, you could share your personal User Manual… you do have one of those don’t you? If you don’t, start by reading this by Cassie Robinson.
  2. Start with realistic expectations. The new person will need some time to understand the context of the organisation, so if they’re sensible, won’t be making any dramatic decisions. However, you need to realise that they’ll be looking for some quick wins to build credibility and momentum. Think carefully what you can do in this area and make suggestions. Bear in mind that the new leader will be triangulating what you say with others, so don’t use it as an excuse to get your pet project higher up the agenda, as that will only backfire.
  3. Don’t expect your structured preparation to be enough. If you’ve shared your documentation, it will raise some questions. Do anticipate being challenged and your previous decisions questioned — that’s just the new leader testing if things are stable and in good shape or need some attention.
  4. Provide feedback as early as you can. Most leaders will appreciate some honest constructive feedback on how they’re doing, what the mood music is. Remember, even if they don’t say it or show it, they’ll be experiencing all kinds of emotions, including impostor syndrome, and feeling the weight of expectations from their new boss. They won’t appreciate gossip, or comments that feel like there is an alternative motive. If there is a problem with communication styles or expectations, then say it early. The reception will tell you a lot about the leader and how working with them is going to be.
  5. Don’t blame them for their appointment. You may not like the decision to create the post if it is a new one, or you might not agree with the decision to appoint this person. Just remember that neither of those situations are their fault. It’s time to get over that and focus on things that are now within your control.
  6. Like it or not, you’re under scrutiny. If your new person has done their homework and done some kind of transition preparation, then they’ll be assessing if the team has the skills, attitude and capability to be part of the future they’re envisaging. In the First 90 days book, Watson suggests leaders categorise their team members into a) keep in place b) keep and develop, c) move to a new position, d) replace (low priority), e) replace (high priority) and f) observe for a while. Be aware that something like this (even subconsciously) will be taking place very early on, so take steps to make sure you’re in the right group.
  7. Remember that their style may adapt. The new leader will not be expecting to treat each area in the same way. Watson suggests categorising different work areas into a) Start up b) turn-around c) accelerated growth, d) re-alignment and e) sustaining success. Some explanations of those categories are available online, and the leader may have other models in mind. It is worth bearing in mind that how they operate when they consider a situation to be a turn-around will be different when they feel it is now in sustaining success mode.
  8. It’s time to share success. A leader coming in feels the pressure to get some early wins. You feel the pressure to demonstrate to them that you’re a valuable part of the future. That sounds like a win-win if you treat it with the right attitude.

Final Thoughts

This has been my attempt to summarise my experience over the various roles I’ve held over the years from both sides of the coin. That’s probably the key. Make sure, whichever side of the transition you’re on, it is worth seeking to understand where the other person is coming from. Happy transitions!

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Andy Callow
Andy Callow

Written by Andy Callow

Husband. Dad to 3 smashing lads. Cub Leader. MAMIL. CDIO for Nottingham University Hospitals. Ex UHN and NHS Digital. Views own. Always learning.

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