Does Your Calendar Tyrannize Your Startup / Project / Life?

Plan more effectively by using Conditions rather than Deadlines

Most traditional project management methods (and I include Agile here) are designed to cater to time-conscious requirements. Obviously, stake holders of any project want to know by when they can expect results. They want to be told on which day the project is expected to be finished, and they want actions and milestones to be set at certain time intervals until then. All project activities are then to be filled into the voids between those dates.

Whether the senior exec sets these time frames in terms of weeks and months, or the tech guru in terms of hours and days… the idea is the same: Set time intervals, then fill the spaces in between with work.

The logic behind this approach is that clear deadlines cause workers to organize their own work towards the goal of meeting those deadlines. This allows the project manager and their stake holders to anticipate when certain things happen and eventually when the project deliverable… gets delivered.
As a cute side effect, you can also use tightening of deadlines as a tool to put pressure on people to work faster.

Makes total sense, right? Sure it does.

Except when it doesn't.

Boohoo… So what’s wrong with clear deadlines?

Where this approach is not appropriate is where, honestly considered, deadlines are not actually the highest priority.

Now, think about that for a minute: Think of your little startup or all the other projects you have planned or worked on in the past. How many of those deadlines were put in place solely for the purpose of having some sort of clear date to work towards, rather than because of some external condition forcing you to have it ready on that date? More often than not, wasn't it simply the expectation of someone wanting to see something on a specific date? Wasn't it only the fear of dragging work out for too long? Wasn't it the belief that people would slack off and waste time if they didn't get “hard deadlines” to adhere to?
How many deadlines really had to be set because some external condition, which you didn't have any control over, forced you to set it, say, under the threat of the whole project exploding if you didn't deliver on that date?

My guess is that there may have been some of those fatal deadlines, but on quite a lot of occasions — if not the majority of them — these dates were completely artificial, often to the point of being entirely arbitrary, just to satisfy someone’s need to see exact dates on a report. Tell me if I’m wrong!

Misguided Priorities

Think about what you’re doing to your project: If you force work to be arranged and organized around deadlines where that’s not needed, you are making those deadlines the highest priority of your project. More than that: You’re making them the goal you’re trying to achieve! Not high quality work, not the validation of the strategy, not the user experience or monetization, not the value that will be provided to customers.

No, you are setting arbitrary calendar boxes with X’s in them on the very top of your objectives.

If you have worked in any mid to large size organization — frankly, if you have worked with any project manager or executive before — chances are you are currently shouting at me, with sad indignation, that usually you don’t have a choice, because that’s what is expected of you.
I know exactly what you mean, because I deal with this every single day myself. As with any change in methodology, you won’t always be able to push them through, because it’s not always up to you.

But sometimes it is. Certainly in your private life, but also when you are just starting to plan your new startup, your new life goal - whatever it is that will require planning and for which you are in charge of doing said planning. Sometimes it may also be possible to combine the conditions approach with some hard deadlines where they are unavoidable. There is no conflict here, just a trade off which you may or may not have to concede to, and which can still yield you some benefits. As always in life: do the best you can with the powers you can take.

Conditions vs. Deadlines

So I am not saying that deadlines are always bad. Don’t get me wrong, there a number of reasons why you want to keep deadlines for your project or at least some work streams and tasks:
Say, a public announcement was made by your CEO with a date, and so you’re bound to it now. Or maybe there is a legal deadline by which you need to deliver a report, or market forces make a certain date the most feasible one (seasonal holidays for example). All of these are external forces that may set deadlines for you.

However, in the absence of such forces, you’re free to organize for success instead of calendar days, with your primary objectives as the milestones to work towards and not any given month or week or day.

When do you start developing? On 1st April? When the design requirements are finalized, that’s when.

When do you start marketing your pre-launch campaign? 31st July? No: when the social media accounts are in place, when the target market is defined and the marketing budget is signed off.

When do you release your product? 15th Oct? No. You release when the testing has completed and bug fixes have been ironed out, when the launch campaign has reached a defined level of engagement, and when you have bought a box of Cuban cigars.

I think the idea is clear:
While you may have to work with inevitable deadlines in some cases, and with pre-defined time boxes in others, you should always determine whether crucial decisions are not better made based on properly defined conditions, rather than random dates. It’s a small shift in your mind set, but potentially with a huge impact on the quality of your work, your confidence when you deliver it, customer satisfaction and growth afterward and eventually the success of your project!

In one sentence:

The success of your project rarely ever depends on when it is completed, but rather what you deliver and how you deliver it.

Getting the What and the How right should always be your main focus! The When is not irrelevant, but it should merely inform your project — not govern it!

How to get Started

Here is a quick starter guide to using terms of conditions, rather than time, when planning your project:

1. Get your goals and objectives right first!

Start by doing a proper analysis of what you’re trying to achieve in the end, and then break that goal down into no more than a handful of milestones that will lead you there.

Question to ask: What is the final outcome everything else should work towards, and what are the 2 to 4 biggest steps towards that goal?

2. For each milestone, define a set of conditions.

Be precise! These will be your tick boxes which will lead you to consider each milestone as completed. Your list of conditions replaces what used to be your deadline, so be sure that they are just as definitive! Take your time doing this step, consider all tasks and variables you can anticipate. These are your positive conditions.

For example:

• Development of all enumerated core requirements
• Successful testing of the delivered code and UI design
• Social media accounts and strategy ready

Then do your best to think of possible issues and hiccups that could prevent you from signing off that milestone, in one word: risks. They are your negative conditions. I like phrasing these in terms of questions, because it sounds more demanding and requiring this way, but that’s arbitrary and just my personal preference:

For example:

• Are all critical bugs fixed?
• Have we received the funding in our account?
• Has the pre-launch campaign achieved 1000 sign-ups yet?

You get the idea.

Again, none of this will be particularly new to experienced project managers. We’re dealing with requirements and risks all the time, don’t we? And if problems lead us to push deadlines out we will do that, too. Traditional project managers are not strangers to flexible deadlines and taking conditions into account.

The difference is the very nature of the decision points you’re setting during the planning phase. It’s a shift in focus: away from reaching certainty by date, towards achieving certainty by condition.

Question to ask: What tick boxes need to be checked before I can move on to the next stage?

3. Estimate, in very rough terms, how long each milestone will take.

Hold your horses, we’re not looking for deadlines here! But of course we still want to have a rough idea of how long things will take. The trick is to stick to reasonable estimates on the scale of months, maybe weeks in some cases, but not any more granular than that.

Secondly, look at dependencies between different work streams and tasks, and take them into account. Make sure your milestones don’t get held up by unnecessarily waiting for tasks to be completed which could have run in parallel had you planned them differently. The super power of ignoring the calendar enables you to focus entirely on the effect your activities will have (rather than when they need to be completed by), and on finding connections between tasks and coordinating them accordingly.

Questions to ask: How long will each milestone roughly take, and how can I save time by coordinating tasks that depend on each other with those that don’t?

4. Adapt dynamically.

Be prepared to amend your list of conditions as you go along, based on new information or issues you encounter etc. That’s totally fine! One nice side effect of not looking too closely on the calendar, is that you won’t feel particularly guilty when you need to move tasks around or when unanticipated issues hold you up for a few days or weeks… Doesn't have to bother you at all, since you were only estimating anyway and you’d rather get it done right than quickly. Because you would, wouldn't you!

5. Plan for Failure.

Now, obviously there is a limit to this leniency towards yourself and your project team. Things like scope creep and never-ending deluges of problems can break your project’s neck without you noticing. And you may end up keeping your project alive artificially, when actually you should have cut your losses a long time ago.

Luckily you are already in a good position to handle this also: By now you will already see that these problems are just more risks which you can absolutely account for by using clearly defined conditions. Go ahead and include a few conditions for the decision to call it quits.

Bonus Tip: Try to imagine precise Yes/No questions which practically force you to admit failure when there is certainty that you should.

For example:

• Have we definitely run out of funding?
• Has the product validation shown that there is enough of a market? (Define “enough” in precise numbers!)
• Will we be able to deliver by Christmas? (If indeed such a deadline is inevitable for your project. Do make exceptions for deadlines when your project’s nature depends on it)

The Mindset

I want to lose a few more words on this. Watch out, we’re getting a bit philosophical now:

I’d like to encourage you to spend a few moments to consider the point beyond work and formal projects. Are you unnecessarily obsessed with the calendar in your private life, too? Do you organize your life goals according to years or maybe even your own age?

By 35 I want to run my own company.

Why 35? What makes that age different to 34 or 36? And if there is no material difference than why would you purposefully plan to wait for the right age? Stalling? Fear of making the first steps maybe?

Think about it: Even if you say you don’t consciously wait “for the right time” to make your move, in practice you do it all the time: Think of New Years resolutions, for example. Why does it matter when a new year starts? Why do you wait for the 1st January to start changing your life (if indeed you do at all)? Why not September 5th? Why not tomorrow? Why not right this minute?

Why not (and this is what I’m getting at) when you’re ready?

You plan to start a new fitness regime to lose weight? “Well, it’s in the middle of November, let’s make it a new years resolution.” Well screw that! That’s completely arbitrary and nothing but a stalling tactic!

You want to work in your soul-sucking job “only until I have 5 years under my belt, to gain the experience. then I’ll move on to better things.” Really?Let’s be honest: You said 2 years when you started four years ago, didn't you? It’s not the number of years that count, it’s whether or not you have learned all you want to learn from that place, and done all you wanted to do there.

So why not make such decisions based on formal, time-independent conditions instead?
Why not create a master list of conditions for the most important and most grandiose goals you have, break them down and start working towards ticking them off, without ever referring to any specific point of time?

Because you fear you won’t get started at all unless a deadline looms over your head? Since when have you ever not found a good reason to push deadlines back? Hell, 99% of the time those reasons are A: bullshit anyway, and B: would never have been necessary had you not spent years stalling by pretending to prepare for that special date that you marked down on your calendar as the start of your wonderful new life, which… for some mythical reason… has to wait for January 1st.

I have yet to fully commit to that new mindset myself, but it’s been a revelation for me. On numerous projects and personal undertakings I have already been able to save a lot of time which I didn't know was locked up on calendar grids. I gained more confidence on deliverables knowing that I had done everything that needed to be done, in just the right way, exactly when it was needed (rather than on some arbitrary day), and so I baked my cake and ate it too: Less stress and better quality work, all within at least the same time frames as if I had worshiped on the altar of the deadline, but usually much sooner.

Now, I shouldn't have to mention that you forego deadlines at the risk of your inner lazy bastard taking charge. Clearly if your motivational level depends on having deadlines and they did indeed prove helpful in the past, you need to find something else to motivate you. But hey, you’ll get help for that somewhere here, too.

Conclusion:

Free yourself from the prison of the calendar and start living in the moment!

Ok, that may have gone a little overboard. But I’m sure you understand. Don’t wait for certain dates to come along: Instead properly plan your moves for when they are possible, and then just make them.

You will know for certain when they are possible, if you have defined a clear set of conditions you can work towards, ticking them off at any time in your life, in other words: when you’re ready.

You will find that in most cases the right time is as soon as possible.
And that, where it isn't, it doesn't matter.