The Eye of Sauron

Even before getting into management, I’m sure you’ll be able to recall the moments that you were under intense pressure to deliver.

Sometimes this pressure can come from anticipation: your team just happens to be responsible for delivering the most important new feature for the company this year. It’s being announced on stage at an event that’s already booked. Argh! Pressure to deliver can also come from catastrophe: parts of your infrastructure may not have scaled as expected and are continually on fire, and unless a new solution is developed, your customers are going to go elsewhere.

In these moments, you’ll have felt what I like to describe as the gaze of the Eye of Sauron. Yes, that flaming, piercing stare of the Dark Lord from the top of Barad-dûr in Mordor. (If you have no idea what I’m talking about, have you never read or watched Lord of the Rings? Go and do that immediately!) Whichever way you turn, the entire business is looking toward you. It’s uncomfortable. You can feel the heat. There are emails, chat messages, ticket comments, interruptions in person, you name it—it’s constant and stressful.

• “Is it looking OK for next week?”
• “Our clients are asking for an update. How’s it going?”
• “Is it fixed yet?”
• “Can we not put more people on this?”

Depending on your mindset, you can turn these tough situations into a challenging but rewarding experience for your team, or conversely, you can totally fumble. Handled correctly, you’ll be looking at career growth. Handled poorly, and you may find the next high-stakes project goes to another team instead.

Warning Signs

You’ll know that the Eye has turned its gaze onto your team by a number of cues that begin to become more frequent and intense.

• Stakeholders show increased interest in your project. You’ll have to bat them away, rather than ask repeatedly for them to turn up.

• Senior members of the business begin to probe into the status of your project at every opportunity, such as when you’re grabbing a coffee in the kitchen or walking down the hallway. You may have never spoken to these people before. Why are they talking to you now? Why is the head of sales so keen to be involved?

• Your boss, or boss’s boss, is being more direct and intense with the progress of your work. Why do they care more than usual?

• You’re noticing how your upcoming feature is being hyped internally and externally. It may now be perceived as the headline launch of the year, even though that was not apparent when you started the project. Why is the business sending out animated teaser tweets when the UI isn’t even designed yet?

• Or, quite simply, everything is on fire and the platform won’t work unless your team digs their way out of this hole. The support ticket queue is getting bigger, and bigger, and bigger…

Regardless of how the situation has unfolded, it’s important to increase your vigilance and take extra effort to manage your and your team’s way through this period of heightened pressure. Handled deftly, you’ll fully own the tough situation and have something to celebrate once you deliver. You’ll also earn the team some much needed breathing room afterward.

Under the Gaze

OK, it’s crunch time. The deadline is next week. It’s looking 50-50. What do you do? Are you feeling the heat? Although the increased pressure will make your job harder, there are some principles that can help you through these intense and difficult periods. Try to ensure that you’re applying them daily, through your discussions, meetings, and decisions.

• Align the team: When you’re under the Eye, your team will probably know. But if they don’t, or if you’re purposely shielding them from knowing, then that’s a bad situation to be in. Utilize the pressure in a positive way: align the team around what they need to achieve, make sure everyone understands how to succeed, and then facilitate them moving toward the goal.

• Over-communicate: At times of immense pressure, you’ll want to increase the visibility of what the team is working on. On top of your usual way of demoing your work, consider writing a weekly (or more frequent) update to stakeholders. You could even record a short video if it’s quicker. Depending on the size of your company, a weekly newsletter to the wider organization might be suitable too. Either way, you’ll want to make it absolutely clear what you’re working on, how you’re progressing, and any key decisions that you’ve had to make.

• Invite responses and feedback: Frustration can be prevented if you open up a clear channel of communication for others to use. Make a chat channel, mailing list, or similar so that curious and restless minds have a place to interact.

• Release frequently: Since your cadence is of utmost importance, ensure that you’re releasing as frequently as possible so that your stakeholders can follow along with your latest builds. The more time that you have for feedback in stressful situations, the better. Don’t keep code held back until the deadline; it just makes the event more stressful and the resulting mega-merge and big-bang release might cause all sorts of bugs. Use feature toggles, keep shipping to production, and tell people where they can look at the new builds. High-performing teams continually ship.

• Be pragmatic: As dates loom nearer, or as the system continues to ignite, you’ll need to make pragmatic calls on speed of development, quality of the code, and creation of technical debt. As much as it can be painful for idealists in your team, you’ll likely end up shipping some shonky code to get the work over the line. However, make note of every hack you put in so that you can tidy up and refactor later.

• Lead from the front: As a leader, you need to set the example for the rest of the team. Put in the work. The hardest projects can become career-defining moments. Own them and be there.

A successful high-stakes project can be fantastic for you and your team: you’ll bond through difficult times, further strengthen your trust and rapport with each other, and you’ll have something big to celebrate.

When the Gaze Is Averted

Let’s assume the pain has passed and you’re in the aftermath of the marketing launch for your new feature. Retweets are pinging off everywhere, the company blog posts are churning out, and you can hear the salespeople ringing the bell again and again and again.

However, what you do next is very important for the morale of your team. Consider this: Glastonbury Festival takes place on a dairy farm, and occasionally the land will have fallow years that allow the ground to recover after all of those cows and people have been traipsing all over it. You need to do the same with your team, even though they haven’t had to endure people dancing on them and being eaten by cattle, although it may feel that way after a deadline.

Here’s how you can round off a tough project and allow some time to recharge:

• Celebrate: This is one of the most critical things. The team has worked extra hard and they’ve met their commitment. Take them out for lunch, or drinks, get some cakes shipped out to the office, put on a gaming night-–-whatever makes them happy. Make sure that you say thank you for what they’ve done.

• Tidy up and clear down technical debt: As the deadline approached, a whole bunch of little shortcuts may have been taken: a hack here, a missed unit test there. Put aside the next sprint to refactor and tidy up at a more leisurely pace, while fixing any production bugs if they arise.

• Do self-guided project time: Time can also be put aside in the coming weeks for some self-directed learning. Allow the team time to experiment and to learn something new. This change of pace and direction puts some mental space between the last project and the next one.

• Reflect: Arrange a project retrospective [DLS06] meeting. It’s a focused way of reflecting on the whole process and discussing what could be handled better next time. Even if the project was run perfectly, the project retrospective is an opportunity to mentally close the current book before opening up the new one.

• Plan and regroup: Take some time to think about what’s next. Are there any initial explorations that can be picked up? Is it time for a design sprint [KZK16]? It’s time to start the discussion, to think about some initial planning, and to get excited about the future.

It’s safe to say that—like any period of crunch—intense periods of work are not sustainable. If a team finds themselves under the Eye too often, it’ll cause burnout and attrition. There may be greater problems with the company if it’s stress after stress after stress.

This may be unavoidable at a startup, but that’s an exceptional circumstance: those that are there are fully committed to the challenging ride. But at a larger company, it’s important to consider how projects and expectations can be managed to allow different teams to feel the heat of the Eye in an alternating sequence as time progresses, allowing the other teams to temporarily shift down a gear and regroup.

For example, it’s advantageous for your marketing department to space out product launches to maintain a steady flow throughout the year. Why not take advantage of this? Your product organization and your engineers can balance these intense periods of contraction with periods of release and recuperation.

As a manager, you should also actively fight for after-project space for your teams if the business doesn’t give them the opportunity by default. When a big project is over, push back on demands to create the room for the rejuvenating activities in the previous section.

It’s a marathon, not a sprint, after all.