The Money Files

Lead by example

Provide emotional support and guidance

Empower teams to take ownership

Encourage open communication

Here in the northern hemisphere the evenings seem to be starting earlier and earlier, and the mornings are much darker. I don't know about you, but I do certainly start to feel less inclined to bounce into work when the sky is grey and it feels like I'm not spending any time in daylight.

On reflection, I think I'm most creative during the lighter months because I can go for a walk in nature. I can have the windows open, I feel like there's an abundance of fresh air and space for thinking. Somehow, being wrapped in my warmest clothes and sitting in my shed/office wearing fingerless gloves doesn't quite give me the same conducive environment for creativity.

If you are feeling the same, here are 5 suggestions that I am going to try to help me feel more creative and to inspire some creativity in my team.

1. Host a mini idea jam

What about hosting a 30-minute brainstorming sessions on process improvements? You could take part of your regular team meeting to pick a process and talk about the kinds of things that work and don't work and what you would like to do differently.

2. Revisit the backlog

Turn “someday” ideas into real experiments. I have a very long To Do List of ideas that I keep in my personal project management software and it's about time I clear them out so that I either take action on one or two or delete some things.

You could do the same at work with your development backlog.

The other thing I'm going to try to do along the same lines is to revisit my pile of books that I have not read and pick something that I'm going to start reading. This year I've read a lot less management and leadership books and a lot more fiction and while I love fiction, I do still need to stretch my horizons by challenging myself with new ideas.

3. Learn something new together

Try an online course or skills swap. Perhaps your organisation has online courses that you can take or access to a subscription service where you can work through online training materials. I know that learning online is not quite as good as meeting up and having the whole in-person experience but it is a fast and simple way to take yourself out of the day-to-day and into a new world of skills and put your brain to use.

If online training isn't your thing, consider signing up to attend a webinar or go to a conference.

4. Change the scenery

Move meetings outdoors (warn people so they can wrap up warm!), or just change your virtual background for fun.

5. Reflect to reset

Use retrospectives for deep learning, not just quick check-ins. How could you re purpose these sessions so that you get to the bottom of a real problem? Use tools like the 5 Whys to dig deep into one particular problem instead of skimming over everything quickly and highlighting lots of issues. Maybe offer to run a retrospective for another project manager or another team so that you can see if their challenges are the same as yours.

It might be harder to kickstart creativity during the winter months, but your creative skills are still there. You just have to create the opportunity for them to shine.

In the Northern hemisphere, we’re going into hibernation mode. The weather might be getting colder but the deadlines are hotting up as we approach year end. It’s always the same: leadership teams trying to get projects done before the end of the year, often for no real reason other than it’s an arbitrary date and it lets everyone start fresh in January.

However, if your financial year finishes in December, there could be good reason for trying to get everything done.

At this time of year there are also other distractions: people taking time off for holidays and the festivities. Here are 6 practical strategies that you can start using on your project to finish the year strong.

1. Plan for the holiday exodus

Map out who’s away and adjust your project timelines early. One of the problems I have found on projects is that I am not always told who will be on holiday because the individuals working on the project do not directly report to me. Check in with their line managers or ask each individual directly about their plans to be away over the holiday season.

2. Freeze your scope

Literally. Stop adding features or deliverables! When you get change requests, put them on the back burner until the new year. That will protect the capacity in the team in order to complete the work that you already have in your work stack.

3. Front-load work

Get critical tasks done before festive chaos hits. Even if you are not expecting chaos, you could still be caught off guard by key stakeholders being out of the office or decisions taking longer because decision makers are not around.

Try to get decisions documented and agreed as early as possible so that your team is not held up.

4. Automate handovers

Prep notes, shared docs, and checklists. If you have anything to hand over this season, make sure you're doing the prep work for it now. That also means making sure your project filing and archiving is up to date. Saved down any attachments from emails tidy up your SharePoint channels and make sure everyone is using the document storage the way that it should be used.

5. Celebrate early wins

Bring in treats or plan some virtual thank-yous for the team. This year my project team is celebrating in November because December is too busy and it's hard to get people to have the opportunity to meet up. If that feels like it will be the same for your team, consider moving any festive celebrations earlier in the year or pushing them to January. January often has the benefit of being cheaper as well!

6. Plan your restart

Schedule a January reset meeting before everyone disappears. Whether that is a lessons learned from a project before you will forget what happened, project scoping or a quarter one planning session, book the time now before all those recurring meetings start dropping into calendars. While you are at it, set up your steering meetings, any other governance meetings, regular project team meetings and anything else that needs to be in the diary on a recurring basis so that your team project sessions have protected time as you go into the new year.

What else do you do at this time of year that helps you keep everything on track to end the year in a good place?
 

I know we’d all like to rely on our PowerBI or Tableau reports, or whatever data source you use for tracking business metrics, but those reports are only as good as the data that goes into them.

That goes for our project management tools as well. If you’re looking at a resource chart trying to work out how to manage capacity over the coming weeks, you’d better be looking at the right inputs. When the underlying data is wrong, it can throw off your scheduling.

But why is data wrong in the first place? No one goes into work and knowingly types in incorrect figures just to make your day difficult. If you’re worried about the integrity of the data, or you want to do an audit check, or even just highlight the importance of getting it right to your team, here are some places you can look.

Human error

Let’s start with the most obvious: Incorrect data input by project team members can lead to inaccuracies in schedules, budgets, and resource allocation. Manual errors in data processing causes more headaches, in my opinion, than anything else.

While we’re on the topic of how humans type things in, let’s talk about inconsistent data formatting. Without standardised data entry methods, inconsistencies such as different date formats or unit measurements can impact data integrity.

Software Errors

How much downtime does your project management tool, or any other data repository that you use, have? How often do you have to raise tickets?

I heard about one team who had been successfully navigating around a bug in the system they used, and talked about how they were managing as if it was a badge of honour – don’t do that! Raise a ticket with the right support team and get it fixed. You never know what kind of impact a bug is having behind the scenes.

Even the best project management software may experience a glitch from time to time that could mean you lose data or it gets corrupted. This can happen when you are syncing data or updating project information, for example importing a spreadsheet from one system to another.

Sometimes we also see issues where multiple users are trying to access or modify the same document or data set where version control hasn't been used. That gives you multiple versions of the same information and no one knows which is the correct one.

External factors

Sometimes it's factors beyond your control that cause problems with data. If you have a network failure, for example, and you're in the middle of doing a data sync, that might affect the inputs. Even hardware failures, the blue screen of death, or losing a USB stick can cause problems (not that you store anything on external drives, right?).

Data integration

In my experience, one of the biggest issues with making sure your data is correct across all systems is how the interfaces work. If you are building interfaces between various systems you have to make sure that the testing is adequate. Whether you are integrating your project management software with financial planning software or a resource management tool or whether you are taking project data out of a scheduling system and putting it somewhere else, it has to be accurate.

Another issue is where the data is being exported from one system in one format and needs to be in a different format for another system —this is particularly relevant with dates.

Identify which system is the single source of the truth and make sure the integrity of that is maintained.

What other issues do you have with data integrity and how do you get round them?

It’s the time of year where people are thinking about how well projects are performing. (Actually, isn’t that all year round?) Which means it’s health check and ‘look back’ time for lots of project managers as they evidence what they’ve done all year and how it has made a difference.

A health check is a useful thing to be thinking about as it shows how the project has performed and what areas you might want to focus in on as you move into 2026 – for this project or for other projects.

However, I know a lot of project managers avoid them because they feel like they will uncover too many skeletons in the closet – there’s too much scrutiny on what might have gone wrong. No one wants to intentionally put themselves in a position where poor performance or bad choices might point the finger of blame at them.

Putting that aside, if you can reframe a health check as a positive way to reinforce what is working and focus in on what is not, they are a useful exercise. As a team leader, you can talk to your team about running reflection sessions to dive into how the project is going.

When to do a health check

There is no ‘right time’ to do a health check but here is when I would be scheduling one:

• Mid-project reset
• Change in leadership/sponsor
• Post-crisis or post-pause

Or at any other time where it fits your governance model.

What to cover in a health check

In a health check, you’ll be looking at scope, schedule, budget, risks, stakeholder satisfaction, team morale and anything else you think might be relevant to help understand project performance.

Tools and templates

You probably have all the right tools and templates already. Check out your PMO document library for:

• Simple scorecard
• RAG review
• Short-form survey that you use with stakeholders and team members to get feedback

How to run it

Keep it short and constructive. You don’t need to spend ages planning for it, or ages holding it. The notes and write up should be short and to the point, highlighting areas to continue and areas to switch up and try something new.

Involve neutral facilitators if needed. Sometimes (I’d say all the time) we are often too close to our own projects to be able to see what is going on in an objective way.

Use it to align and re-energise. The whole experience should leave the team feeling lighter and more able to focus on what is coming up for project milestones – it’s not ideal to leave with a huge To Do list of improvements that you won’t have time to implement. Aim to get two or three things out of it that you can do easily to help the team move forward and improve project performance. Any more than that and chances are you won’t ever reach the end of the list. You’ll spend more time trying to implement process improvements than delivering the project, and that isn’t a good result for anyone.

Remember: Work with the team to reframe health checks as maintenance, not judgment. They should be something that easily slot into the project schedule and are a positive experience with some great learnings that you can implement quickly.

Leave the deep dives for full-on audits and keep quick health checks part of your retro routine!