How not to suck in your first 100 days in your new job

Andy Callow
8 min readNov 19, 2024

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The Final Hurdle?

So you’ve been brilliant so far, you didn’t suck at writing your job application, you didn’t suck in the interview and you didn’t suck at negotiating your offer, so now you can relax right?

WRONG!

Now is the time to prepare for not sucking in those important first few days of your new job!

A Caveat

This material is drawn from a talk I did at the CIO Watercooler event in Manchester in November 2023, called “How not to suck in your first 100 days as a CIO”, which in turn is drawn heavily from the Michael Watkins book The First 90 Days. The material in my original presentation is slanted towards senior digital jobs, but I think much of this is pretty universal.

Iteration

Over the past few years I’ve started different jobs. If I compare how it felt in those first 100 days against how much preparation I did, then there is a big correlation between the two, such that by the time I started my latest job, things were working pretty well. There is a marked contrast between me starting at NHS Digital and starting at Kettering General Hospital. So what happened at this point?

The Book That Started It All

As I was preparing to start at KGH, my good friend and wise egg Ian Thomas recommended The First 90 Days by Michael Watson, having used it when preparing to start a significant new role.

Image source: https://www.amazon.co.uk/First-Days-Updated-Expanded-Strategies/dp/1422188612

At the very start of the book it says, that

75% of senior HR leaders agreed that​

​“Success or failure in the first few months is a strong predictor of overall success or failure in the job”​

​First 90 Days — Michael D Watkins [p1]​

I think this is one of those books that you have to properly engage with the process in order to get most out of it. It is peppered with exercises that force you to think carefully about how you’re preparing. It is so easy in books like this to skip over that, but for me, that’s where the big value comes from.

The book has 10 sections as below:

  • Prepare yourself​
  • Accelerate your learning​
  • Match your strategy to the situation​
  • Secure early wins​
  • Negotiate success​
  • Achieve alignment​
  • Build your team​
  • Create alliances​
  • Manage yourself​
  • Accelerate everyone

So at this point you could stop reading this and go and buy the book, but just in case, I’ll set out a few areas of the book where I hope I can add some practical examples of my response to the book exercises, drawn from my most recent new role.

Prepare Your Self

In preparing to start at NUH, I reflected on my time at UHN and asked myself the following questions:

  • What I did well​
  • What I could improve on​
  • What I’d do quicker and​
  • What I’d do differently

I wrote up a page for each of these items and tried to prioritise the most important ones. I ended up carrying those pages round with me in paper form for the first 6 months, checking every week which things I’d ticked off that I intended to.

Martin Sadler

It also helps to have some time with someone who you can bounce ideas off. I spent time with Martin Sadler, who shared his thoughts on starting a new organisation and the questions he asks when joining a new organisation. He’s turned a lot of his wisdom into an excellent book — Aspirationally Idle, which is recommended reading for digital leadership roles.

Accelerate Your Learning

Watson stresses the need to acquire the necessary knowledge of your new role as quickly as possible. Based on my preparation, having now joined the organisation, I created a set of structured questions that I asked all Heads of Service to fill in:

  • What services do you deliver? ​
  • To whom?​
  • ​What do they think about the service?​
  • ​What else do I need to know? E.g successes, concerns, risks​
  • ​What would you like to deliver that you can’t ​
  • ​What do you wish you could stop?​

I also asked them to create a “blob” diagram with a one-sentence summary for each blob. This material will help you create a high-level service catalogue.

Negotiate Success

One of the important things in arriving in a new role is to ensure that what you’re working on aligns with the organisational strategy and what your boss wants you to be working on. In senior roles, when joining a new organisation, you need to give yourself some time to assess the information you’re acquiring and use that to form some early opinions and then check out with your boss if your direction of travel aligns with them. This is about demonstrating that you’re doing the right stuff early.

After 2 weeks in, I shared my initial view with the CEO, setting 5 high-level observations emerging. For me this was:

  • highlighting the historical underfunding — triangulated using Model Hospital, which showed that only two organisations spent less on digital, data and technology per FTE.
  • That there was no clinical-communicable EPR strategy in place, so colleagues has no hope of a better future of the massive number (429) of systems they were called to use.
  • That some of the basics were not in place — for example that NUH had never achieved the DSPT and a set of metrics measuring performance was not in place.
  • That the information and reporting was in a reasonable state, with a good Integrated Performance Report (see page 99) in place, but large numbers of reports which uncertain use.
  • I also identified early that there was no prioritisation method, so the team were trying to do too much. I explained how I was going to spend my next few weeks testing out these emerging views and using it to formulate a prioritised set of actions.

During this time I was asking loads of questions — maintained via a sharepoint spreadsheet and I also met with key suppliers. At about 4 weeks in, I shared the emerging views in a workshop with Heads of Service, setting out ​what I thought we do well and high level reflections on where there was scope for procurement and proposed three priorities.

This process continued. At about 12 weeks in I shared these evolving and iterated views with the Digital and Data Strategic Committee, then a month later with the Board and then started formulating an action plan at a second workshop with Heads of Service. The essence of this period was to keep acquiring information, whilst being open about emerging views, to test out my views with others. The trick I feel in this period is to avoid the temptation to leap in and try and solve problems, where I think it is vital to maintain a high-level view.

Manage Yourself

​During this period it is really easy to get bogged down and keep going down deeper and deeper rabbit holes. One way the Watson book talks about this is to ensure that you’re managing your own physical and emotional energy levels. Besides getting out on my cycle, my approach to this is to engage in regular reflective practice.

There are a number of templates to use, but these are not a bad set of starting questions to use daily or weekly as you see fit:

  • How do you feel so far?​
  • What has bothered you so far?​
  • What has gone well or poorly?

It is really easy to canter from week to week in a busy calendar, without stopping to think about what worked or what didn’t. And when starting a new job and feeling the pressure to make an impact makes this even more stark. Taking a moment to look back in a structured way gives you that opportunity. The way I do it is writing a weekly blog in a format known as Weeknotes. After doing this for nearly 6 years, I’m strongly of the opinion that this provides me with such personal value, that I’d still do it, even if no one read it. Honestly, how much time do you spend at the end of the week thinking what went well and what could be done better?

Why do it:

  1. It creates a Progress Account — How many times have your arrived at your quarterly objectives review and wondered what you have been up to in the past 3 to 6 months. By being structured and intentional in how you reflect on your work, you’ll have a ready made repository of progress.​
  2. This practice aligns to the agile manifesto. “​At regular intervals, the team reflects on how to become more effective, then tunes and adjusts its behavior accordingly.”
  3. It encourages accountability — either to self or if you publish it publicly, those who follow you. ​

So you could just write this stuff down and put it on the fridge door, or share it with you line manager, but my view is that putting things out there in the open is a way of you being prepared to be held to account by your colleagues, which I think is a good thing.​ Not least as Working in the Open is enshrined as #9 in the NHS Design Principles

Make things open: it makes things better Share your learning. Share your work. Be transparent in your design decisions. Be accountable and have confidence in your solutions.

Go For It

So having done this, you now should be set up:

  • You know your team, the work they do, their strengths and areas for development
  • You’ve got a set of high-level priorities that you’ve tested with your boss, your peers and the teams
  • You’re looking after yourself

There’s a lot more in the Watson book and my recommendation is to properly engage in the exercises as part of your preparation, augmented by a few of these tips. My observation is that very few people do even some rudimentary preparation before starting a role, let alone take a structured approach to when they are there, so even if you only engage in part of this, you’ll help yourself and increase the likelihood of success in your new role.

After all, you worked hard on the application, interview and negotiation, why wouldn’t you put the same effort in now you’re in role?

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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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