How big is the breadbox?

A highly critical aspect of your leadership job is being able to make predictions. Sometimes, the most difficult of these can be in making project estimations. Your ability to intelligently provide an overall estimate that comes close to reality will do much to solidify or liquify your management career. There are so many different aspects to consider, so many different variables in play, and so much pressure from above to do an absolute maximum performance with a minimum of expense and time, that these experiences will leave you wondering what you ever thought was enticing about a management job in the first place.

If you are working in an industry that can take advantage of an AGILE process, you can avoid many of the problems involved with estimating huge projects. But, for now, let’s assume that’s not the case. Over the years, I’ve found that there are really a few key principles to keep in mind that can help make the job much easier, and help you deal with the pressure that always comes to “do more with less.”

We’ll start by covering the cardinal rule of guesstimating… overestimate, and overdeliver. That means, give an estimate that you can beat (by just a little bit), and bring in a product that rocks!

The first important aspect here is leaving plenty of room for your team to adequately get the work done. It can be very tempting to give estimates that make it look like your team can perform at super-human levels, and maybe they can from time to time. But, doing that too often will lead either to failure or mutiny by your team as they grow to resent the never-ending pressure you’re placing on them. They might step up to the plate for you in an emergency situation, or at some time when the company might have a major opportunity, but eventually they’ll think you’re a loser for constantly making them work 80-hour work weeks so you can come off as some kind of hero.

Even if you think you’ve left sufficient time in your estimate to allow the team to accomplish the goal without absolutely killing themselves, you probably still need to provide an even bigger safety margin. Everything takes at least double the time you think it will anyway.

The best technique for estimating the time it will take your team to accomplish a task is for you not to estimate it at all. Let the team give you the estimates. Start with the front-line folks who will actually need to do the work, and ask them for their best estimates. They’re the ones with the most intimate knowledge of what they’re being asked to do anyway. It is also usually true that workers will give themselves tougher goals to achieve than you would assign for them. Whether based out of ego, a desire to over-deliver, or maybe they know how to do something better than you do (hard to believe, I know), whatever they come up with is something they feel comfortable with.

At this point, that guy (or team) owns the estimate. As long as you don’t go mess with the assignment, he should be absolutely committed to coming through for you – no excuses. If that means he needs to work a little extra time, okay. Keep your eyes on the progress, and make sure to refresh his memory if needed. There is absolutely no excuse for someone making his own estimate that a job can be completed in 10 days, and then having it take 10.5 days. If, at the end of that 10th day, you see that guy heading for his car at 5pm, you should congratulate him on having the job done on time. If he says, “Actually, I just have a few more hours to do and should be all done by lunch tomorrow,” you have every right to turn him around back to his desk. He couldn’t find an extra few minutes a day to get it done? Not acceptable. Major project slippages don’t happen all at once. They are the result of many little slips all piling up on each other. Mind the little things.

In the next installment, Scotty comes through for Captain Kirk again...

Caulk, not concrete!

Let's continue the discussion around making good decisions.

Sometimes, it's not just about making GOOD ones, it's about making QUICK ones. It is amazing how long people are willing to merely let things ride, despite massive evidence pointing to a need for change. Whether in regards to a particular personnel problem, a process problem, or something inherently wrong with a product, humans do tend to like that path to effort minimalization.

You must remain as vigilant as possible on your own. But you can profit greatly from input from your team or the occasional outsider who, benefiting from having that fresh pair of eyes, simply asks, “What’s up with that?”

Through whatever mechanism, when you detect things going wrong, do not delay in finding a better way. Although we certainly want to avoid extra work when possible, things like this fester quickly, and before long, you will be dealing with a monstrous ravine requiring a dump truck full of concrete to fill it, rather than applying a little caulk to a crack.  Do it now!

When you decide to make modifications, ensure that you’re doing them for the right reasons, and with the right evidence supporting the need for the change. I have definitely been guilty of making some changes, or being talked into them (still my fault), where the situation didn’t seem to require modification at all. Things had been working wonderfully. True, I could have been deluding myself, but after collecting additional information, it still wasn’t clear why the proposed change would improve the situation further. The lesson learned is that old adage of “if it aint broke, don’t fix it.”

However, there is an interesting corollary to remember as well – “If it didn’t work the first time, why would it work this time?” This is somewhat akin to Einstein’s definition of insanity being “doing the same thing over and over while expecting different results.” If you had a process that you stopped using, or a person that you managed out of your company, and now you’re considering going back to that process or rehiring that person, be sure to ask yourself “why?”. What’s going to be different this time? Will the process be used in a different environment? Will there be better people executing it? Has this person changed or grown somehow? Whatever the case, be certain that you’re not expecting things to be different just because time has passed.

Finally, when the changes are implemented, do not take your eye off the ball! Be especially wary of the potential for the cracks to begin developing anytime you are intentionally making changes. In these cases, you're already focused on it, so you have your best opportunity to closely monitor how the new things are working. Watch carefully until you’ve seen evidence that your improvements are, indeed, improving things.

Ebony and ivory... bad choices

Black and white. Both have their uses, but not so much in the process of making productive and effective decisions. You need to be prepared for a distinct lack of problems that result in a choice of two polar opposites like “we either do X or we do Y.” Everything turns into a dingy shade of gray. And that's not a bad thing! There’s almost always a way to find something in between X and Y that results in a better final outcome.

Here's what’s painful.  It’s much easier to settle on X or Y, and not spend the extra brain cycles trying to figure out if there isn’t something a little gray that might be more attractive. And, as humans, we’re certainly known to enjoy the path of least resistance. But this is a pain you must accept. In my experience, black or white answers will usually be insufficient to solve a problem, or they will be outright wrong. If you or your folks seem to be setting something up as an X or Y decision, step back and ask if there really isn't anything else somewhere in between that might make things even better. You'll surprise yourself with the new creative ideas you can come up with.

Also, remember this. Over the lifetime of a particular project, its success will be determined by how you and your team handle a plethora of decision-making opportunities. You’ll have hundreds, or even thousands, of decisions that will plow the road to eventual victory or catastrophe. A few of these decision points will be biggies – major choices with monster affect. But the vast majority will be much smaller issues that need to be handled almost daily throughout the project's life.

Which of these, the bigger ones or the smaller ones, have a more urgent need for your thoughtfulness and ability to bring focus? Answer: the smaller ones! The really big ones are going to get everyone’s attention. People will so clearly see the issue’s significance that the pot will boil over with attention. But, it’s those hundreds or thousands of smaller issues that others might not be so interested in that require your assistance. It is more likely that the project will fail from a “death by a thousand cuts”, since each of those little wounds won’t attract the same level of interest as the big issues.  Be on the lookout for those!