The chief executive's last 100 days

This resource sets out learning from a series of interviews with CEOs at various stages of departure from their roles – from just about to hand their notice in, in their last 100 days, to having left up to 12 months ago and in a position to reflect back. The CEOs interviewed come from different charities (different sectors and sizes, at different stages of their lifecycle) and are en route to different places (to retirement, to another CEO role, to a portfolio career). 
Many of the experiences reported were against the backdrop of CEOs running an organisation in the time of the Covid-19 pandemic – working virtually or in a hybrid way, which has made a difference for them and is reflected in the resource.

Quotes from the CEOs are included, but the identities and conversations have been kept confidential for obvious reasons!

The resource also draws upon our search of the available literature, and links are provided throughout to some of this (limited) literature which you may find useful to support and extend your thinking.

Choosing when to go is (mostly!) the CEO’s prerogative. This is where the reason for leaving and desired next steps post departure can really change the characteristics of the ‘last 100 days’ and will influence the time available to plan and to solidify legacy. Amongst those interviewed for this resource, there was a wide variety of circumstances:

• Those able/wanting to be flexible with their notice period (going on to retirement or a portfolio career, with choice and the willingness to be flexible over departure date)
• Those moving on to another job and/or wanting to keep to their contractual notice period
• Some were contractually on three months’ notice, some on six months
• Some gave 12 months’ notice, some six, some three
• Those with a senior leadership team able to step up; those in smaller organisations without any such capacity/capability.

There are a range of views emerging from the conversations:

• With three months’ notice, the recruitment of a successor is just about possible, but having a period of overlap between outgoing and incoming is highly unlikely (unless the successor is an internal appointment or currently not in paid work); appointing an interim is an option – either a member of the senior team stepping up or an external interim appointment
• Six months’ notice is seen by the majority of those with this experience as “undoable” creating a vacuum that’s hard to fill; “it’s a real challenge to maintain the energy” and “it’s more about fear based decision making on the part of the board than the right thing for the organisation”. One departing CEO (who was taking up another CEO role) found themselves getting drawn into decisions that their new organisation needed to make during this period, but also being expected to get involved with decisions in their current organisation that they suggested their successor should have been making.
• Having an interim, or having the senior team step up is seen as a positive: “most things won’t grow unless there’s space; the successor would find it helpful to see how people have responded in an interregnum”
• Four months is seen as a reasonable time by some – to have a good ending, maintain energy, plan for an interregnum, know the details of the successor and start to talk them up and pave the way.

Those interviewed for this resource had suggestions about the sequencing and typically found the task of breaking the news took about five days (elapsed time):

1. Tell the Chair first (depending on the quality of the relationship); a number had frank and proactive discussions with the Chair about their future plans well before actually handing in their notice, but others found it hard to say “I’m looking for another job” and said nothing at all until it came to resigning
2. Give the Chair time to think about how they want to handle next steps both by way of the announcement, and then to organise and hold the transition and the appointment of a successor (and in recruiting the successor “they are about to make the biggest decision they will ever make as Chair”)
3. Take the Chair’s lead on telling the board
4. A number then told their executive assistant before anyone else
5. Then the senior leadership team
6. Then together, they made a plan about telling the rest of the staff group, volunteers and key external stakeholders (with the latter, most CEOs had a list and in one example there were 100 people on it!); action the plan – where possible make staff communications face to face. For more on this see the section 'Theme: It’s about intentionally shaping your legacy’
7. Publish a written communication and public statement (including tailored for social media)
8. Make the news public.

All those interviewed emphasised the need to design the communications – both the message and the medium:

• Be clear about the rationale
• Honour the past and shared achievements
• Look forwards and be optimistic – sell the benefits and opportunities for the organisation
• Set out what’s going to happen to ensure a smooth transition – give people a sense of the timeline – but be flexible and adjust to events as necessary
• Create opportunities for people to be involved in the transition; one example was at the second meeting with staff (after breaking the news), to do an exercise together exploring ‘what qualities do you want your new leader to have?’; the outputs were summarised and used in the recruitment material thereby helping to engender a feeling that staff had had real input into the leadership transition.

Having open conversations about succession is not only good for developing talent but creates a climate of trust, with ‘no surprises’ and takes away fears – normalising something that can generate uncertainty and upset. Succession planning has a focus on identifying potential replacements and preparing them for the role through development activities; it is a board responsibility for the CEO role, and boards are usually interested in succession for the whole senior team.

CEO succession planning should be integrated with wider organisation development:

• A structured transparent process, integrated with talent management activities and leadership development (all with a focus on developing future leaders equipped to deliver the organisation’s strategy)
• Both about knowledge building within other roles, and about developing experience through things like job swap, job rotation, stretch assignments, coaching/mentoring.

There's more here from the CIPD factsheet on succession planning.

And an introduction to talent management from the CMI here.

And advice from McKinsey’s:

1. On developing your leaders as part of succession planning
2. And perspectives on succession planning from a start-up founder about how to plan a leadership transition emphasising that laying the foundation for a successful transition can take years.

Recognising the importance of the Chair/CEO relationship to organisation effectiveness, many Chairs and CEOs have purposeful conversations about their relationship and the A Question of Balance guide from the Association of Chairs was cited as a good basis from day one for developing the relationship and as part of this, discussing succession.

This 2015 article from 'The Guardian' newspaper shows how the then Brook Chair and CEO co-ordinated their plans for departure to ensure it worked both for them as individuals and for the organisation.

A key task that needs to be planned for is the recruitment of the successor – a board responsibility but one where there is usually some involvement by the outgoing CEO.

Whilst job descriptions and person profiles should be kept up to date, the departure of the CEO is a great opportunity to refresh these for the CEO role, especially with regard to defining the knowledge, skills and behaviours required in the post holder for effective delivery of the future strategy.

Often the nominations committee of the board drives CEO recruitment, advised by the incumbent CEO to a greater or lesser degree. It’s the board’s responsibility to appoint the CEO and is unusual for the incumbent to play a role other than providing input re role and necessary qualities, helping develop a recruitment pack, insights into the challenges of the role etc. (“providing a view based on a rationale and evidence”). But we heard from more than one CEO that they had had to support, in some cases, "push” their board to kickstart the recruitment process, helping with a timetable to maintain momentum ("working in a consultancy way with the chair – a change of dynamic”).

For one it was quite a painful process (“I thought the board would step up more”). Many boards have had no experience of recruiting a new CEO and can find the responsibility somewhat daunting (“recruiting a new Chief Exec was much harder than they expected even when using an agency”; “my board realised they had a limited view of the CEO role and that was mostly the outward facing part”).

Help the board unpack the job in practice (not just what’s in the current profile) and ensure it reflects the needs of the present and future organisation. Importantly, support the board to ensure that the recruitment and selection process is as fair, inclusive and equitable as possible.

For most of those we spoke to, it was hard to dissociate leaving the CEO role with responding to the demands generated by the Covid-19 pandemic (one felt it had “confounded my ability to be clear” by making it difficult to judge what to re-engage with and what to leave as everything was so connected).

Several spoke about balancing overseeing continuing change in the organisation ("things we must resolve”) but not doing so much as to impede the changes their successor would likely want to make (“be as settled as possible but allow room for manoeuvre”, “ticking off the stuff that is a responsible thing to have sorted out before we hand over the baton”). But some also mentioned the potential danger of “stalling the organisation” if the senior management team starts to say “we won’t do anything on this until the new person starts” thereby effectively paralysing the organisation until the new leader starts.

Several mentioned developing a “transition plan” to guide the process and prioritise.

Maintaining momentum during the last 100 days is understandably impacted by whether the successor is an internal (interim or permanent) appointment or one recruited from outside the organisation. Having the former was reported to “take the pressure off” by knowing there was someone to hand over to; someone who brought an understanding of the particular complexities of the external and internal environment; someone to actively develop in the run up to the change of leadership - and required managing a reset of the relationship.

The Bridges Transition Model helps organisations and individuals understand and more effectively manage and work through the personal and human side of change. Bridges’ model identifies the three stages an individual experiences during change:

1. Ending what currently is
2. The Neutral Zone
3. The New Beginning

The Neutral Zone is an in-between time when the old is gone but the new isn’t fully operational - when the critical psychological realignments and re-patternings take place. It is the very core of the transition process. Several CEOs mentioned organising activities designed to support board and senior team engagement during the last 100 days and beyond - building a bridge between their departure and their successor joining - exploring who will do what and when etc. ("filling the space”, “providing reassurance and answering concerns”, “recognising anxieties”) – investing in these key relationships and by engendering trust, helping to provide the seedbed for a new beginning.

The critical relationship between CEO and Chair becomes even more important when the former announces their departure. A poor relationship is unlikely to be reset in the final few months (although the fact of the upcoming departure will influence the dynamic and instil a sense of urgency).

Factors such as how long the Chair has been in the role (and how long they have to serve), context and the challenges the organisation is facing will influence the focus of the interaction in the final few months. Several suggestions were offered as to how to create and maintain conditions for an honest and open relationship between the Chair and CEO during this time:

• Review the structure and focus of conversations with the Chair; agree how to use the time most effectively e.g. one CEO, where the Chair was new in the role, introduced thematic meetings (brand, fundraising etc.) to maximise opportunities to build the Chair’s knowledge; more than one said they prioritised the tactical and operational rather than the strategic
• Respond to what the Chair needs from the CEO during these final months (“how can I support you best?”)
• Identify how the Chair might provide support. For example, by bolstering relationships with key stakeholders
• Consider the frequency of meetings (with most reporting meeting more frequently)
• Build in conversations about your legacy (“stops you having to hide things”); be open and transparent: what’s gone well and what might have been done differently; explore concerns and upcoming challenges
• Help to build a relationship between the Chair and your successor (if one has been identified) by involving them in meetings as your departure grows nearer

Several reported turning to their board more during their last 100 days particularly with trustees longer in the role. Closed sessions (board and CEO only), if not already part of governance practice, provide a forum for open dialogue about challenges and opportunities, reflections on past decisions etc.

A CEO’s resignation understandably unsettles an organisation (no one knows what’s coming next or how things will change).

At the early stage in the last 100 days, there can be an element of denial from the senior team (SMT) (“how will we manage?”) and progression through the classic stages of grief. Obviously, the senior team will have more of a vested interest in the future success of the organisation than the outgoing CEO so a key role is to help the SMT to carry on (“provide reassurance that the walls won’t come tumbling down if, for a period, there’s no CEO in post”).

We heard from CEOs that from the time they announce their departure, so much of their attention is about supporting the SMT prepare for the change, manage their anxieties and concerns. The CEOs we spoke to all took their resignation as an opportunity to help the SMT step up (“I’m withdrawing, and I need to help those left to fill the space”), seeing any gaps as a positive opportunity for development and growth (“to establish their powers”) by, for example:

• asking different SMT members to chair meetings
• encouraging them to build direct relationships with board members (but keeping everyone informed)
• being more externally facing (“go out, be the spokesperson and network”)
• seeking an external mentor
• involving SMT members in the detail of some aspects of their work (“to provide continuity once I’m no longer around”).

One CEO is framing their departure as “what opportunities does this present for you?” and planning a session for the SMT to explore and agree how they want to step up and prepare for the transition.

As the CEO disassociates from the role and starts to transfer power, the SMT will be deciding how they are going to deal with things going forward ahead of the arrival of a new leader.

Several CEOs mentioned observing the SMT getting stronger and more confident during their last 100 days; for some, the urgent and practical need for an organisational response to the challenges of the pandemic united and galvanised the SMT and provided unexpected learning opportunities.

Mark the ending of your CEO role (whether going onto to another or not) in an unfailingly positive way (“I wanted to leave with a good taste in my mouth”):

• Be conscious about emphasising (proactively, consistently and regularly) the positive aspects of your departure; that it’s good for the organisation to be having fresh leadership (“this is going to be great!”)
• Avoid any inference that you are “leaving a sinking ship and going off to a fabulous yacht” or are leaving because of your relationship with the Chair or the staff etc.
• Mention you are sad to be leaving the staff (“it’s a great place to work”)
• Emphasise that you are leaving to join a new organisation, not rejecting this one
• Have a leaving party to provide an important and positive marker of the change (“provide an opportunity for people including yourself to say nice things and move on”)

Your contacts, networks and social media:

• Develop a network to provide a safe space and sounding board to help you explore what’s a good exit from the role. Don’t ignore the personal impact on you (when so much attention is on supporting the organisation to navigate the transition) and find somewhere safe to offload. One CEO decided who should be in their ‘new’ network to support them through their personal transition by creating a “fellows’ network” composed of their ex-Chairs and trusted colleagues. Others mentioned having the support of those who had gone through the same journey particularly helpful
• Consolidate your network differentiating between those contacts you don’t want to lose touch with (“people you will want to make an effort with”) and those to whom you will “put out a general call to on occasion”. Think about how you are going to keep in touch
• Remember to think about what you are going to do with your Twitter handle and LinkedIn profile even if you are taking a break or retiring (“you don’t want to disappear – it’s a risk”)

Harvard Business Review suggests that how you handle yourself during your final months and weeks will have a big impact on how you are remembered. Daniel Kahneman suggests that people’s memories are largely shaped by peak moments (good or bad). In this context, he suggests that how you are remembered will be influenced by how you spent your final days in the role i.e. boasting about accomplishments or showing deference to and respect for the incoming leader.

There is an overarching desire to balance making sure that things are actioned so that the incoming CEO can have their 100 days’ breathing space to get acclimatised and sort their priorities, with not setting them up with decisions that don’t need to be made.

All of these ideas are about ‘clearing the decks’ of anything outstanding but not starting anything major, and are dependent on the timing, the context (e.g. not an emergency) and how long it will be before the incoming CEO starts (avoiding a vacuum).

What to action

• Draw attention to the hotspots in a handover plan (things that might need attention in the first few months)
• Depending on the timing, draft the annual report for last year
• Hold team meetings with staff to ensure that annual operating plans are clear and that people know what is needed of them over the transition period, and that engagement is as good as it can be
• Resolve any outstanding HR anomalies e.g. salary benchmarking
• Sort out those projects and problems that have been hanging around for ages that need tying off e.g. getting funding for a project that’s in the strategy – so that the successor can arrive with everything in place
• Make sure all the policies and frameworks are up to date and clear, especially safeguarding, health and safety etc.
• Draft an induction programme for the incoming CEO including items you wish had been included in yours

What to leave

• Embarking on new relationships / partnerships with key external stakeholders
• Try not to start new things unless there’s a brilliant opportunity and everyone (Chair, SMT) agree it’s too good an opportunity to miss (“from day one after handing in my notice I never took a decision on my own”)
• Leave things that need a fresh eye (some things may need a new person coming in to shift e.g. behaviours)
• Be clear about what you can’t do and will pass on; “don’t try and put a bow around everything”

Some CEOs noted that preparing for the arrival of a new leader reframed the conversation – that it wasn’t just about the board and senior team anymore - but was about anticipating the needs of the new CEO (whether interim or permanent) and prompted reflection on culture (“why it’s a good place to work”, “what we like and want to keep”).

One arranged for a coach to help the team explore culture (“what it is that works?”), helping to form a bridge between the outgoing and incoming leaders. One CEO said that from the day they resigned, they had been planning and thinking “how can I make it as good as possible for my successor?”.

For some CEOs there’s a parallel process going on: the outgoing CEO is navigating their last 100 days, and the incoming leader their first 100.

Practical suggestions to support preparations for the new leader’s arrival include (in addition to handover notes) include:

• Speaking to potential candidates (“no one else can do this in the same way”)
• Preparing to share - “the stuff that’s hard to write down”, “the things they need to know that only you know” - history, relationships, power dynamics (“the subtleties of how the team works together that they would find hard to express”), the key players
• Agreeing a handover of key activities (and starting to prepare handover notes as soon as possible)
• Offering to meet or being available: one CEO suggested meeting at least once before the new leader starts and then a couple of times afterwards. Other CEOs mentioned fairly regular meetings with their successor for a short period and others were surprised that the incoming leader didn’t take up the offer to meet etc. at all
• Introductions (“slowly”) to key players or when an opportunity occurs
• Inviting to key meetings such as a Trustee away day
• Giving up their office as soon as the incoming leader took up the role

CEOs described shifts in their mindset (personal and organisational) from the very first day they knew they were leaving:

Organisational: learning to lead in a different way:

• Initiate a mindset shift (“how do I help the organisation prepare to carry on without me?”). From then on, it’s about learning to lead and manage in a different way: helping to prepare the board and SMT for the upcoming change and support them to be ready to take on what’s needed (“every action, every decision has this in mind”).
• One spoke of being a lot more cautious than they would have been if staying - a sense of wanting to protect the organisation - for its success to continue.
• Another spoke about being 'more visible' and accessible to staff during their notice period (prioritising being in the office as much as possible)
• Prepare for time to speed up - anticipate the last 100 days flying past! ("it went so fast in a blur of busyness”, “I had to keep reminding people that I only had two, then one month left”).  Most prepared a plan for what to do each month in the countdown to their departure to anchor the time available (reinforcing the limited time left).

Personal: looking after yourself:

• Book in time to reflect on how you want your future to be (be it in another role or not). Some on retiring from their CEO role, sought counselling during their last 100 days, recognising fears of status etc.
• Try to build in some time off - you will likely have demands from your new employer to join activities etc. - and time will be very precious (and very pressured)
• Note your mindset shifting (“the weight starts to lift”, “I’m withdrawing and I need to help those left to fill the space”); most spoke of having a clear sense of being CEO to the very last day (“no sitting back, foot to pedal to the last day”, “Third sector leaders put everything into the role – it’s hard to relinquish it but then you start to get excited about the next chapter)”

• Ensure your transition plan (shared with and owned by the board) includes a communications strategy setting out how you are going to inform key stakeholder groups (e.g. those the organisation supports, staff / volunteers, funders and suppliers etc.) about the upcoming leadership transition.
  As part of this, agree the frequency of updates throughout the transition and who will lead on them, including for example how the Chair will be involved
• Undertake an external stakeholder analysis of your key stakeholders (and the relationship they have with the organisation) to ensure you capture those key relationships

On being offered a new role, one CEO was meticulous in drawing up a list of stakeholders to inform immediately (and personally) about his departure, mindful that if they heard the news once it became public knowledge, it would have a negative impact on how they viewed their relationship with the organisation (and its professionalism). This plan - personal contact with 100+ people and completed over a period of five days - recognised how important these relationships were and contributed to the achievement of the CEO’s personal objective of “leaving well”.

Being the founder and moving on
Much has been written about founder syndrome, when a founder struggles or refuses to accept change and becomes a constraint to growth and organisational development. Some see it as being inevitable (and negative) but Rachel Warwick’s experience as the founder of Make Lunch was different and suggests that founders can let go of the organisation they established in a positive way. Rachel founded Make Lunch in 2011 to provide free, hot, healthy meals to children and families who would otherwise go hungry. Rachel recently stepped down from the organisation after overseeing a merger with Transforming Lives for Good (TLG).

Rachel says she always knew she’d move on when the time was right, which in the event came earlier than she’d anticipated, when an opportunity to merge with a much larger organisation, (TLG), unexpectedly presented itself and helped the charity step up to the next level.

Ahead of stepping down, after seven years in the role, she had come to the realisation that she “would be getting in the way” if she stayed at Make Lunch, and the success it had achieved, had outgrown the skills she’d brought and they had identified a need to formalise the chief executive role at that point. “I saw the transition not being solely about me, but about what the organisation needed as it grew. In the end, merging with a much larger organisation meant they didn’t need to recruit a chief executive but going through the process brought clarity and generated an opportunity for merger that might not have materialised otherwise”.

The last 100 days
Rachel experienced a gradual transition out of the role during her last 100 days and recognised a time when she judged that decisions were no longer hers to make, instead directing the team towards TLG managers when they had questions, helping smooth the start of the handover and build relationships.

Working with the team and other stakeholders
Make Lunch was a small organisation – six staff and a very close team – but with a huge reach, working in 100 locations. “I shared as much as I could with the team – as early as possible - about the upcoming change. I understood the sadness some were feeling that Make Lunch would not continue as before - that it was the end of something - but I focused on helping them to appreciate that, within a larger organisation, there would be more opportunities to reach and make a difference to even more children”.

A positive action in supporting the transition and reducing anxiety was for the Make Lunch team to meet with representatives from TLG and together explore those aspects of the merger that were non-negotiable (from Make Lunch’s perspective) and map out how their work was going to look post-merger. This gave staff (who were going to stay) confidence and an input into the change process and, for those who were leaving, a sense that their work would continue.

Rachel was clear with external stakeholders, some of whom who were anxious (“I hope it will be alright!”) and encouraging about the opportunities merger would bring (“keep feeding the kids and all will be ok”). Throughout the transition, she made it clear that the change wasn’t because of her - that she’d not lost the passion for the cause - and stressed the positives of the change.

Marking your departure in a formal way
Rachel gave TLG a DVD of the documentary that had sparked the idea for Make Lunch (and an apron) as physical representations of the organisation and reminder of its origins. She

was invited to return some months after she’d left to speak at their conference and this felt like the circle was complete.

Rachel’s top tip for anyone leaving an organisation they founded?
“Keep separate the passion you have for the cause (which will continue) and your identity, and maintain perspective: you’ll always be the founder but you won’t always be the chief executive. Have trustees who can see the organisation changing and are able and willing to let it move up a step and help it along the journey”.

October 2022

Blog: How to leave a team you lead
Hiranya De Alwis Jayasinghe

Hiranya explores the real example of when she left a team which she had led throughout the turbulent days of the pandemic.

She explains the processes that she actively chose to implement with her team to get them involved with the transition and to end on the best note possible

How to leave a team you lead

Published October 2021

This resource was co-produced and written by CCE's Fiona Ash and Caroline Copeman.  Published August 2022.

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