Beating Deadlines 101: How to Outsmart the Corporate Obsession

18 atomic tips any manager can use, starting today.

“We have a real business to run, so we have to be serious. We have to set deadlines. Otherwise, we are a joke. Enough with this agile nonsense.”

Ever heard this? I have, many times.

But deadlines are 99% fake except for the rare legitimate ones like Black Friday or Tax Day.

The unfortunate reality: fake deadlines drive today’s corporations.

They are the lie we tell ourselves to seem in control despite our complexity and uncertainty.

• Complexity integrating new and legacy technologies
• Uncertainty on how to create true fans of our customers
• Uncertainty of how long it will take to build the right solution
• Complexity in the human dynamics of those crafting the product

Deadlines seem like something solid to hold on to in this perfect storm.

In turn, many managers believe they have no option but to set them.

And here’s why:

• Sales needs to make a promise
• Customers need expectations set
• Vendor contracts need start and end dates
• Yearly budgets need an investment duration
• Open-ended projects are simply not good business
• To continue investing, we need to understand how long until it’s done
• Return on investment forecasts require a start date for benefits to flow

The voice in your head tells you, “Managers must manage. If you can’t control when something will be done, what good are you?”

Not having a deadline gets perceived as vague and, to be honest, weak in most organizations.

You won’t survive in today’s managerial landscape if you can’t set a deadline and drive a team to stick to it. The ugly truth is that many teams also don’t survive a deadline. And many products share the same fate.

So, here we are in quite the pickle.

Deadlines don’t breed success, yet they drive today’s corporations

They get used improperly to motivate. They get used to sell ideas. And they get used to construct a fiction that complexity and uncertainty don’t exist, so you, your department, or your team can survive another day.

And they have dire consequences.

• Fear of failure
• Betting on hope
• Disengaged teams
• Compounding risk
• Dampened learning
• Unsustainable workloads
• Plummeting transparency
• Planning and status theater
• No space to improve or iterate
• Turf building and blaming (as a survival mechanism)
  

Despite all this, deadlines appear here to stay.

Yet, in my view, nothing adds more waste, demotivates more teams, or drives more products into the ditch.

And this is ultimately disastrous to your career as a manager.

Let that sink in.

18 Atomic Tips To Outsmart The Corporate Deadline Obsession

We have now established the cancerous nature of deadlines (especially the fake ones).

What if there was a way to get what you want as a manager, catapult your career, and avoid the curse of the deadline?

There is hope.

The most savvy managers obsess with creating an environment where deadlines don’t matter.
 
After 20 years in the trenches, I’ve gathered 18 tips from the actions they take to outsmart deadlines. They have uncovered the secrets of true agility. And now, you get to take a peak.

Hint: It’s not about getting more disciplined and working harder. Rather, it’s about doing the things that make deadlines not the driving force.

As it turns out, agility and deadlines can actually be friends.

Legitimate (not fake) agility is your best bet to beat legitimate (not fake) deadlines.

Actually, the enablers of agility are the key to delivering value sooner, deadline or not. But let’s be honest, 99% of organizations who claim to be agile, aren’t. These companies are right in thinking agile can’t work with deadlines.

The agile theater most know well won’t save them.

So, let’s stop the skit.

Are you motivated to tackle the deadline dilemma and reap value sooner while respecting people?

Know this: by activation of the 18 agility-based tips below, you can make not having a deadline be seen as a sign of strength, not a weakness.

But likely of even more interest to you, as a manager, delivering value sooner will secure your future.

Sounds awesome? Let’s dive in to learn the secrets for outsmarting the deadline.

Tip 1: Be aware of the true nature of product development.

Let’s stop the charade—the path of product development is not knowable up front.

We must stop treating it as simple and certain, as if we can predict its output, outcome, and impact. You will only be frustrated by trying to predict the scope, time, and cost needed to create a winning product. And it’s not just you. No one else has a crystal ball either.

Treat any product prediction up front as highly suspect and as an amateur move.

Tip 2: Make experimentation safe, even when it fails.

The product path is not clear, and it’s not straight.

So, expect teams to experiment to emerge the route they should follow. Remember, they are creating a path where none exists. This means they may take a step and realize it’s a dead-end. If you expect missteps, it becomes safe for them to take a step, fail, back up, and try again.

So, encourage your teams to keep steps small, and don’t freak out when the step is a misstep.

Tip 3: Test ideas with your customers before, during, and after delivery.

An idea with no customer is like a seed without soil.

Help ideas take root (or not) through continuous team and customer engagement. Ruthlessly discard the ones that don’t produce fruit. Nurture those that do.

Help teams validate or kill ideas faster with rapid, frequent customer feedback loops.

Tip 4: Focus on achieving value instead of meeting deadlines.

Customers don’t care if you delivered by a deadline. 

They don’t care that you delivered everything you set out to do. They don’t care if you deliver it all on time. They see no value in how much effort you put in or the experience you have. If your product doesn’t delight them, you’ve lost them.

Make something that people need. 

Nothing more and nothing less will make a difference.

Deadlines simply don’t inspire greatness in teams. But knowing and connecting with what your customer needs does.

Teams who know their customer can get to value sooner.

Tip 5: Commit to goals and keep dates, scope, and plans negotiable.

A worthwhile goal is a problem to solve, not a prescribed path to follow.

I’ve learned the hard way that no plan survives the reality of the terrain. So, don’t lock in dates, scope, and detailed plans up front at the moment of highest ignorance. Instead, embrace learning.

Plan to change the plan.

Tip 6: Co-create long-term and short-term goals with your teams.

Far-off goals, crafted in a boardroom, fall flat.

Thud.

But achievable goals generated with a team have strength. A goal a team has had a hand in shaping has its attention. It becomes its baby.

Nothing channels focus and builds autonomy like a team that truly owns its goals.

And with goals, thinking big and acting small keeps the momentum flowing.

A long-term target keeps teams oriented. And short-term goals in the direction of the far-off target harvest value along the path. Accomplishment builds energy.

A team’s inspiration comes from small wins on goals it owns.

Tip 7: Remove waste in your process so you can reduce your lead time.

Most teams work in a system riddled with waste.

• Hand-offs to other teams
• Producing more than is needed today
• Defects they have no time to stop and fix
• Extensive waiting for decisions to be made
• Having to follow outdated, extra processes
• No authority to take action without approval
• Juggling too many things in flight (goals, features, tasks)
  

So, as a manager, it’s your job to start removing this cruft.

Help your teams capture value sooner (deadline or not) by clearing the things they can’t remove.

Tip 8: Try something simple to learn instead of creating a detailed plan.

Ignorance is at its zenith before work begins.

Yet, before work starts is when detailed plans and deadlines usually get created.

Know this: a detailed plan at the moment of highest uncertainty is a plan to fail.

So, resist the urge to create a detailed plan and timeline until reducing the knowledge gap. The best way to do this is to place many small, cheap bets to learn. Breaking through the knowledge threshold reveals the right path you should take.

Plans and deadlines don’t drive action. Rather, action, and the learning from it, drive the plan.

Tip 9: Involve stakeholders in building the product instead of promising a date.

“We don’t set deadlines. But would you like to join us on the journey and shape a solution that precisely solves your problem?”

This is the statement made by an organization that had instituted a no-deadline policy. Stakeholders would ask, “When will you be done?” And every manager and team in the 400-person department would answer like that.

This single act generated the best business and technology partnership I’ve ever seen.

Two things happened:

1. Stakeholders started engaging with the teams and helping to shape the solution.
2. Slowly, but surely, due date requests evaporated.
   

When stakeholders become part of the solution, they don’t have to rely on deadlines for control.

They can instead focus on steering based on evidence to their desired destination.

Tip 10: Involve your team in brainstorming ideas to meet goals.

The feature factory will not save you from the doom of deadlines.

Instead of handing down a baked backlog to a team, involve them in solution ideation.

Teams have a unique perspective. They are closest to the work, and they know what is realistic and what is not. Applying their feasibility lens to the conversation generates stronger options.

This is how the magic happens.

When a team ideates, builds, and delivers end-to-end, they find the right value sooner.

And they do it with more pride and fewer missteps.

Tip 11: Have teams own the creation of their estimates and delivery forecasts.

99% of the time, teams get handed a deadline they had no hand in creating.

Deadlines set in a vacuum demotivate teams. And teams fight back against any unrealistic constraints placed upon them. Eventually, though, they give up the fight and accept their deadline-driven fate.

And no disengaged team survives for long.

Instead, involve the team in estimating and forecasting when their work will complete. Apply a cone of uncertainty to any forecast. And don’t expect precision.

Those who write the plan don’t fight the plan, and, plus, it’s based in reality.

Tip 12: Improve your team’s learning velocity (build, measure, learn loop frequency).

Aim to learn fast and cheaply to remove your risk.

In other words, don’t wait until solutions are fully baked to get feedback.

And teams should show their early experiments to customers and stakeholders.

These initial, cheap versions are easier to throw out if they are wrong. Remember, product development is complex and uncertain. The faster the feedback loop, the faster you find the right thing to build (and what not to build).

Learning speed gets you to value sooner.

Tip 13: Engage teams with customers and stakeholders directly (no go-betweens).

A proxy adds handoffs and all the waste that comes with them.

Teams who don’t know their customer and stakeholders don’t really know what they are doing. They are simply doing what they are told. This lowers autonomy and adds significant risk to value flow.

Instead, match teams directly with their customers and stakeholders.

Connecting teams to the source emerges the right solution sooner.

Tip 14: Coach teams to use evidence gained by action to refine delivery forecasts.

Plans and forecasts should not be a one-time deal at the beginning.

It’s better to expect continuous planning. Know that your teams will learn from each step they take and build that into their next step. As a result, plans will evolve. The real plan may not match the deadline, but this is the transparency you need.

A fresh, evidence-driven plan gives you the raw reality to steer the ship around obstacles so you don’t crash and sink.

Tip 15: Build goal-oriented product roadmaps instead of feature and deadline-driven roadmaps.

How many times have you created a roadmap riddled with features and deadlines?

I see these roadmap fairy tales all the time.

A roadmap with specific solutions and timeframes is no more than smoke and mirrors. The detail they provide ignores the inherent complexity and uncertainty. Remember, no one can determine exactly what will be delivered and when.

So, you should instead build a goal-oriented roadmap.

1. Use now, next, and later for timing.
2. Identify customers to target and problems to solve across the time horizons.
3. If any solutions are listed, call them options, keep them high-level, and isolate them to the Now bucket.
   

Focus your roadmap on solving problems instead of predicting the future.

Tip 16: Allow teams to prove they can speed up by self-improving the way they work. Don’t ask them to set stretch goals.

Stretching a rubber band past its limit will cause it to snap.

A stretch goal is a deadline by another name. It’s an ask to do more in the same amount of time. Stretching pushes a team to do more than they have proven they can do.

Instead, promote continuous improvement and make space for teams to get better.

When teams have the space to improve how they work, they will. And they will become more effective. No stretching needed.

Tip 17: Aim to reduce and simplify output and maximize outcomes.

Start with good. Engage with your customers. Evolve.

You need to accept that you don’t know the answer.

Finding the solution that makes a difference requires trial and error.

1. Start with the essence of a solution, no adornment.
2. Get user feedback.
3. Relentlessly pivot based on feedback. Throw out what doesn’t work. Keep what does.
4. Evolve detail where needed, no more.
5. Get user feedback and refine until desirable. Stop.
   

Engage with your user before, during, and after you build a solution. Evolve from a place of good, and stop when good enough to delight.

The best solution you can imagine may not be what the user needs in the time that they need it.

Tip 18: Create delivery forecasts with date ranges to reflect uncertainty.

Precise dates are precisely wrong.

Learning evolves as you take each step. Before you take any steps, your learning is zero. After you take many steps, your learning builds your confidence. Use the evidence from each step to reflect your forecast certainty by using ranges.

Here’s how this plays out:

1. Use a large range around your forecast at the beginning (pro-tip: the range is so high up front, this forecast is usually not worth the effort).
2. Gradually, reduce the range around your forecast as you gain knowledge.
3. Only give a precise date after you are finished.
   

Exact dates imply certainty, so you should certainly avoid them.

Bonus–Tip 19: Just stop setting fake deadlines to spur performance.

If you practice the other 18 tips, you won’t need fake deadlines.

Bye-bye, deadlines.

A fake deadline is a whip to drive teams to do more, better, faster, and cheaper. But the tips in this post will get you to value sooner, without the whipping. A team with high levels of autonomy, mastery, and purpose is a much better bet.

The motivation to do more with less comes from within, not from a deadline fiction.

So, first practice the other 18 tips. Do any one for a quick improvement. Go all in to create a movement. Either way, you will soon be comfortable leaving fake deadlines behind.

Do it for the good of the team, product, customers, stakeholders, and, ultimately, you.

THANK YOU!

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