The Money Files

Last time I wrote about managing the project and the team during the end of year countdown and the holiday period – today I’m thinking about managing stakeholder expectations.

Let’s face it, our stakeholders are also distracted by holidays, year-end processes, and vacations, and we still need to keep them engaged and informed about project work. Here are four practical strategies to keep everything on track at this time of year.

1. Understand their availability

Are they taking time off? You can ask – even senior leaders are likely to be scheduling a break! Their availability (or lack of it) might mean rescheduling project board or steering group meetings, and it’s better to know about that early.

Discuss realistic expectations for responses and turnaround times during December – if you’ve got key members of the project team out of the office, you might need a little longer to get back to them, or they might need to deal with someone else on the team. Pass along any contact details or make introductions beforehand so they know who to talk to – and so that person is aware that senior leaders may be reaching out while they are covering for a colleague.  

2. Prioritise critical deliverables

Make sure you and your stakeholders have a shared view of what deliverables are critical for this period. Define what must be completed before year-end and what can wait. That might already be clear from your project plan, but if you are working in an agile way or in an environment of high uncertainty, it would be worth reiterating what is possible before the end of December.

If you can, think about how you can build flexibility into timelines and make those suggestions. The stakeholders might not understand what goes into completing a task, so they might see something as do-able when in fact it is not. If your office has a mandatory closure or an IT change freeze, that might also eat into the time available to complete work.

A clear list of urgent deliverables and non-urgent tasks can help everyone prioritise, and it’s likely to look different from the last time you created one, because that’s life!

3. Communicate early and often

This is not going to come as a surprise, as communicating early and often is something you’ll be doing all year round. However, at this time of year, there can be a lot of communications, a lot of deadlines and messages can get lost.

Check in to see how they would like to be updated and if that is different from the rest of the year, update your comms plan so you don’t have to ask again next year.

4. Think about stakeholder fatigue

We all need a break, right? Stakeholders are no different. If you’ve been powering on waiting for the holidays, so have they. Think about how you can keep stakeholders engaged during a busy time, maybe cutting the length of meetings, sharing papers earlier so they can read them before a meeting or sending out weekly email updates instead of having status update calls.

Don’t forget to say thank you! We tend to schedule time with the team to celebrate achievements, but our senior leaders were also part of that, so recognise their contribution too. You might be the only one who does…

Good planning and communication can help manage stakeholder expectations even when times are busy – and the run up to year end is definitely busy!

Is your team a remote or hybrid team? It can be challenging to keep projects moving with the same pace during the holiday season, when availability and communication can be limited. Here are a few tips on how to stay on top of your project deliverables over the holidays.

1. Establish availability and schedules

Encourage colleagues to set clear expectations around holiday availability and working hours. For example, they can set out of office messages and identify a delegate in that message so that people know who to go for when they are unavailable.

If you have limits on how many people in the team can be out of the office at the same time, then make sure these are clear and communicated. A project team holiday calendar can make it clear when people are off (although you’ll have to get them to fill it in… always a challenge). There might be times when holidays are unlikely to be approved, for example over a go live period, so flag that in advance so that anyone who needs to book holiday can do so with enough notice.

2. Communicate across time zones

Your remote team might not include people in different time zone, but given that there are multiple time zones in Europe, the US and Australia, as well as elsewhere, even if you are working solely within one region it’s likely you will have colleagues who are keeping different hours to you.

If the holidays mean your working hours are different, make sure everyone knows this. Check that people are aware of the most appropriate ways to stay in touch. For example, Teams is the best way to get me, even when I’m travelling or otherwise out of the office, because it’s on my phone and I literally can’t escape it!

(That’s not to say you should be working on your time off, but if you are working remotely, make sure you can still be contacted.)

3. Adjust project timelines

You might want to adjust the project schedule to account for reduced productivity during December. I know no one wants to admit to being less productive in December, but if you take out time for school concerts, longer, social lunches, plus the impact of the weather and so on, you might find that productivity dips a little. If you’ve got the flexibility in the plan, consider using it.

4. Maintain team morale

The flip side of a productivity dip is a task surge. I don’t know about you, but the last few years have seen me working even more than usual during the run up to year end as we try to get deliverables completed in year.

So consider what you can do to keep morale high, if work is going to be tough. That might be a team celebration (virtually – there are lots of options you can do remotely including quizzes and games) or other ways to connect when team members are scattered and less available.

5. Ensure project continuity

Most importantly, make sure that there is continuity and that the work continues, even when key team members are out. For example, make sure that your documentation is up to date and that knowledge-sharing has happened to avoid bottlenecks. Use the pre-holiday period to review plans with the team and make sure that everyone knows what they have to do.

Whether you are a remote project manager or working with a remote team, it is possible to navigate the holiday period and keep your projects going. It takes a bit of extra effort, a little more stakeholder engagement and a lot more forward planning, but it pays off to know that you can balance work and life, have a wonder holiday period and also stay on top of your work without burning out.

How do you do it? Share your tips in the comments below!

As a project manager, there are two types of self-management I have to do.

Proactive management is looking ahead, making sure I know what is coming up.

Reactive management is addressing the challenges of the day, fire-fighting and being asked to do something on top of my existing workload.

Proactive management

I think proactive management is where most of us should be spending most of our time. We should be looking forward, using risk management, horizon scanning or whatever you want to call it to get a good idea about what’s coming.

For example:

• Future projects that your manager is going to assign to you.
• Upcoming milestones that you need to check in on and make sure are on track.
• Risks that have a close proximity that need active management.
• Engaging stakeholders so they know what is coming (with the goal of reducing ad hoc queries or report requests).
• Big meetings or meetings where you have to prepare documentation or submit proposals/presentations/papers in advance.

These are all things that we should know are happening or about to happen and then we can plan our time appropriately around that.

We find out about these things by staying curious, asking management, putting time aside to review the project schedule alone and with the team, and listening out for things that might be a problem. The more you spot coming, the more you can work around it, or into it so it can be handled at a time that suits you – not at the last minute creating a fire you have to run around and put out.

Reactive management

It’s much harder to manage time when you have to spend it reactively responding to whatever is dumped on your desk that day. It could be a project task that someone else was supposed to do but hasn’t, and just needs to be done, it could be new work to do with your project (like setting up a meeting with 10 attendees that has to be at a particular time but no one has calendar availability at that time… don’t ask me how I know!).

Other examples would be things like:

• A supplier letting you down and not delivering goods on the specified day.
• Someone being off sick and not being available to complete a task that’s on the critical path.
• A senior executive asks for an ad hoc report on project progress for a committee meeting that is tomorrow.

Building resilience in yourself and the team is a good way to manage the short-notice requests and feel more capable of responding in the moment.

In my experience, the better I am at proactively managing upcoming situations on my projects, the less reactive management I have to do – but I know it does not always work that way. Generally, though, the more you can anticipate senior leaders’ needs, complete your risk management actions, identify problems before they become a ‘real’ problem and so on, the less reactive fire-fighting you have to do.

Admittedly, you can’t necessarily foresee that the weather is going to cause problems, or that a supplier might have difficulties fulfilling orders, but if you have identified these are risks, you will at least have (hopefully) spent some time thinking about how they might be mitigated or addressed if they do happen.

Do you spend your time between proactive and reactive management – and is this distinction a helpful way to frame your work? It really works for me, but I don’t know if it’s a common way of thinking for other project managers. Let me know in the comments!

As much as we’d love to have everything working to plan, sometimes we can take some aspects of project management for granted. I wonder how many of these project challenges you have but you haven’t openly recognised within the team?

I don’t want you to have your head in the sand, so below I share 10 things that you might be missing on your project.

(I didn’t want to bury my actual head in the sand, so you got a photo of my feet buried instead! Not quite the same, I know.)

1. Stakeholders are reading your communications

We might believe that stakeholders are reading our project comms, but are they really?

It’s hard to tell, but if you aren’t seeing any action, or people are asking questions you have already answered in your comms, then they probably aren’t.

2. The training you’ve scheduled is enough

I expect it isn’t, even if it feels like it should be. People won’t turn up or won’t use the online training to teach themselves. Plan to have post-launch training support because your users will need it.

3. Your change management plans are adequate

Hopefully they are, but as above, there will always be someone who says they didn’t get the memo, or couldn’t access the materials. Make sure you’ve got post-launch training in the diary as well, and do more change management activity and engagement than you think you should have to.

4. The UAT plans are long enough

UAT is the one thing that gets squeezed in my experience. Add in an extra cycle if you can. It’s easy to take it out – not so easy to squash it back in if you do need more testing time.

This obviously depends on your project – if you are doing something you’ve done a lot before you should have a high degree of confidence in your deliverables, but you might need more if you are working on something new.

5. Risk identification has spotted everything

It hasn’t!

Make sure risks are constantly mentioned in all meetings, and that you are always listening out for what might be a new risk.

6. Team morale is OK

Team morale is something to keep an eye on. The team can get demoralised for the smallest of reasons, from a change not being approved to a reschedule for whatever reason. That negativity can spiral.

Even if things are going well on your project, events outside the project can influence morale, such as a change in leadership, redundancies, an increase in BAU work or pretty much anything else.

7. Benefits are understood

We’d like to think the financial and tangible benefits are understood, but how well have those assumptions been documented? I’ve worked on a couple of projects where we think we understand what we are tracking, only to find that we can’t replicate the exact formula the finance person (who has now left) used, or some other difficulty.

You should be able to answer straightforward benefits-related questions like ‘is this incremental revenue or total revenue’? So make sure you can.

8. There is no conflict in the team

There probably is, but people are too polite to mention it. You should dig for it! Some conflict is healthy so don’t worry about bringing it up.

9. Quality is being managed OK

Are you finding bugs in your deliverables? And more importantly, are you squashing bugs? What are your criteria for exiting testing and how does quality play into that? Ideally, you should have great quality measures, and be performing in line with those, but sometimes project teams get swept up in the desire to deliver and that means some lower-risk bugs are left in for now.

10. There is no technical debt

Are your project deliverables introducing technical debt? Are you breaking things elsewhere or for other teams, or introducing workarounds or degrading the solution for someone else? Sometimes your part of the world might be fine, but a process you’ve implemented ends up in many additional steps or a new report being needed for someone else.

Check that you aren’t creating technical debt by accident – if you know about it, document it and have created it ‘on purpose’ as part of a stepping stone to a different solution, then that’s probably fine.

Which of these might your project be at risk from? Let me know in the comments!

Are you starting a new project? As we get closer to year end, we seem to be starting more projects that will (somehow) finish in-year! If you are kicking off a new piece of work, whether you’re delivering by year end or have a longer timeframe, here are some tips to consider to ensure you are starting off in the best possible way.

Get the right people

First, you need to understand the capabilities required to deliver the project. Then you have to make sure you have people with those skills (or people with the aptitude and time to learn them).

It’s not just about the do-ers. You’ll also need a project leadership team (a project manager, sponsor, maybe exec sponsor and programme manager) who have the skills to lead and are empowered to do so.

Create your Charter

Whether you call it a project initiation document, charter or kick off document, you’ll want something in writing to document what you are doing and how. But the real value of this is in the discussion that you have while pulling together the content. The right conversations are essential to make sure the right stakeholders are involved, everyone is aligned on the objectives and the scope is clear.

Set the tone for the team

We talk a lot about culture and I’ve written about psychological safety before. Start as you mean to go on, so set your ground rules, working practices, terms of engagement up front. Make sure that anything that affects the delivery team involves them (so no setting project delivery dates without the people doing the work in the room).

Set up your document repositories and communication schedules so everyone knows what to expect and where to find the latest information.

Consider risk

As part of your project initiation work, you should be creating an initial risk log. But considering the impact of uncertainty on your project goes beyond that. Make sure you’ve got enough contingency in the plan, especially in the early days until estimates can be firmed up with more data. Make sure stakeholders know about confidence levels and be transparent about what you think can be achieved, so their expectations are managed.

Sort out your governance

Exec confidence comes from knowing the project is in safe hands. Governance might feel burdensome at times, but it ensures the right work is being done by the right people at the right time.

Make sure you know how the project will be held to account, and what the success criteria are. Set up your peer reviews and stage gates. Book steering group meetings and regular check ins. Dig out your reporting templates. These processes will ensure that there is trust in the process and that leaders feel confident that the project can (and will) deliver.

Setting your project up for success is crucial because those early days set the tone for how the work will be done. Spend a bit of time – and I know, you’ll have to negotiate for that as I expect everyone wants the work to have started yesterday – and you’ll have a greater chance of delivering successfully. Good luck!