Setting Deadlines

Deadlines. This is what we're going to be talking about today on this episode of How to Lead, the podcast for CEOs, founders, and leaders of all sorts who want the perfect balance of empathy and authority when it comes to leading their people. My name's Kate Waterfall Hill, and I'm going to be sharing some ideas from over 30 years of working in business and leadership development.

Before we start the show, here's a quick reminder that if you want to know how to become a better leader, sign up to my free weekly newsletter at waterfallhill.co.uk. You'll also find other resources like my book, How to Lead. So let's kick off with my alter ego, Linda, the bad manager and see how she goes about getting her team to meet what she says is a non-negotiable deadline.

This project absolutely has to be finished by tonight. So whether you've got to stay late or not, I don't really care, but I've got to have it on my desk by nine o'clock tomorrow morning. So where are you at with it? Still got a few more bits to do. I'm just going to refine it slightly. Just say it again, it's absolutely got to be done by the end of play tonight.

Well, actually, I don't care if it's, if it's not till midnight, but it's got to be on my desk at nine o'clock. Okay? All right. Good stuff. See you tomorrow. Thanks. Hello? Oh, hi. How can I help? Have I reviewed the project that you submitted at 3 o'clock this morning? 3 o'clock this morning? Um, I haven't actually yet.

No, no. Well, I know it's 4 o'clock in the afternoon, but, um, and I know I said I needed it by 9, but actually my meeting got moved, so, um, yeah, it's not for a couple of weeks now, yeah, so the urgency is slightly off. Yeah, yeah. In actual fact, I'm not entirely sure we're going to use it at all, but, um, thanks for your efforts anyway, yeah.

Oh, it makes you cringe, doesn't it? Linda's way of demanding work on my desk by morning only to not even bother looking at it because the meeting got cancelled It caused a right stare on TikTok when I posted that video, as you can imagine.

I was inundated with similar stories from people with Linda like bosses. Whilst the video might prompt a smile or a wince, it highlights a serious issue that I see constantly in these messages from my followers. The toxic cycle of unrealistic deadlines, midnight oil burning, and broken trust. And let me tell you, this toxic approach does nothing for building relationships and getting people to go the extra mile for you.

I hear from creative agencies in particular, where the leadership teams just can't understand why they're haemorrhaging young talent. But we've always worked this way, they say. When I was starting out, I practically lived in the office. right, and how's that working out for everyone's mental health?

I mean, don't get me wrong, I was there. I was also working all hours. But times have changed, you know, thank goodness for that. Today's workforce, particularly those in the younger generations, often described as Gen Z, although that slightly irks me because I say Zed.

But anyway, they have this radical notion that their time outside work belongs to them. I know, it's shocking, but they're setting boundaries that many Gen X managers find challenging. And here's the thing, these boundaries aren't just good for employees, they're actually good for business.

Let me share a story. One of my old consultancy clients, a particularly creative and industrious CEO, was notorious for his Sunday night quick thoughts that he sent by email. They always somehow turned into Monday morning emergencies. His team was burning out, productivity was tanking, and his best people tended not to stay long.

When I challenged him on this, his response was, But I'm not explicitly asking them to work weekends. Well, the trouble is, that's what people interpret when you send them an email on a Sunday. We worked together to transform his approach, and the results were really eye opening. Here's what actually works when setting deadlines.

First of all, this might be groundbreaking to you, but try asking your team how long things will take. I know it's a bit of a revolutionary concept. We tend to enforce these deadlines because that's how we've always done it. But actually, it turns out that the people doing the work might actually know something about how long it takes to do it.

I get the idea that some people will say a ridiculously long deadline and you want them to do it quicker, but come to some compromise if you can. Second of all, build in some buffer time. Things go wrong, you know, servers crash, people get sick, life happens. Your project timeline shouldn't just rely on everything going perfectly.

That's not planning, that's wishful thinking. Third, and my character Linda really does need to take notes on this, if you set a deadline, respect it. Nothing destroys trust faster than making people work through the night for a meeting that gets pushed back three days. Your urgency needs to match your actions.

You can transform your deadline culture with what they call a reality check framework. Just ask these questions. Is this deadline business critical or is it just habit driven? What's the real impact of moving it by a day or a week or even a month if it's a big project? Who needs to be involved in setting realistic timelines? And what's the human cost of this deadline? The results are likely to be better work, happier teams, and it's proven by experience that deadlines will be met more often. But let's talk about that tricky balance between organisational needs and individual boundaries.

Because yes, sometimes we do have genuine deadlines, you know, clients need things, markets move, opportunities arise. So here's what works. Clear communication about why deadlines matter. Also collaborative planning with buffer time built in. Respect for contracted hours. This is really important. And contingency plans that don't rely on heroic all nighters.

Also, you must give fair compensation for genuine overtime when it's unavoidable. Have you heard of deadline dialogues? These are regular check ins where teams openly discuss capacity, challenges, feasibility. It's amazing what happens when you treat professionals, well, like professionals, dare I say it.

And as for those Gen X managers struggling with their Gen Z boundaries, think of it this way. Would you rather have a team that's fresh and focused and doing their best work during contracted hours or a burnt out group resentfully watching the clock tick past midnight? The truth is sustainable productivity isn't built on last minute panics and energy drinks, it's built on respect, realistic planning and recognition that your team has lives outside work.

Because leadership isn't about demanding what you want when you want it. It's about creating conditions where good work can happen consistently and sustainably. The other element to keep in mind is managing expectations, both with seniors and clients.

I've got to admit, I've been guilty of this as well, you know, promising unrealistic timelines. Maybe it's a client and you tend to say, yeah, sure, two weeks is fine. we know it'll probably take three or even more. Or expecting our team to pull off the impossible just because we're afraid to push back.

The trouble is, unrealistic deadlines don't just stress out your team. They create a domino effect of rushed work, compromised quality, and damaged trust. Instead, try this. Add a 20 percent buffer to your estimates. Account for the real world, whether it's meetings, emails, unexpected issues, and yes, even sick days.

For your team, be transparent. Share the why behind the deadlines and create space for honest feedback. With clients, learn the power of under promising and over delivering, and break down complex projects into visible stages. Don't be afraid to educate them about your process. Remember, saying no to unrealistic deadlines is actually saying yes to quality work, team wellbeing, and sustainable success.

Maybe have a think about your current projects. Are your timelines realistic? Make those adjustments now. You know, your team and your future self will thank you. So next time you're tempted to do a Linda and demand work by the morning, ask yourself, is this deadline serving the work or dare I say it serving your ego?

In summary, then setting effective deadlines isn't about demanding more. It's about planning better and being clear on reasonable expectations. Collaborate with your team on realistic timelines, respect their boundaries, and remember that sustainable productivity beats heroic all nighters every time. The most successful leaders aren't those who demand the impossible, but those who create the conditions for consistent, quality work within reasonable hours.

Sorry, Linda, but the days of on my desk by morning are well and truly over.

So that's it for the topic of deadlines. If you've enjoyed this episode of how to lead do follow for more leadership insights. And if you want a guide by your side, get your hands on a copy of my book, which accompanies this podcast. It's also called How to Lead. There's a link in the show notes.

Please like leave a review and share with your fellow leaders to help spread the word. I really do appreciate any support you can give. And if you've got any suggestions for future episodes, please do let me know. Team management doesn't have to be frustrating. You too can enjoy being an authoritative and empathetic leader.

It just takes a decision to be more intentional about your interactions with others, some great tips for how to influence positive change, and of course, a good guide. Until next time, listen more, advise less, lead well.