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Take off the Cape, Super Yes Man

Topic: Entrepreneur Evangelist | Comments (2)

Posted on February 10, 2010 by admin

As I’ve written before, I firmly believe that entrepreneurship requires a basic level of optimism, simply to get up every day, much less to actually be successful. In addition to being optimistic, successful entrepreneurs also need to have a keen ear for the sound of opportunity knocking — and then rush to answer the door.

Because of this, most of the entrepreneurs I’ve met in my life have had a strong natural inclination to over-use the word “Yes!” And while that word is never intended to have a negative impact, the reality is that it is often the gateway to a slippery slope that no one saw coming. Michael Michalowicz, of The Toilet Paper Entrepreneur, discusses this in his recent post, The Most Dangerous Word In Business.

The scenario that Mike paints is reasonable one, and worth considering. But in my career, I’ve found myself reliving a different version of the same problem. Envision this scenario:

A big client has a new idea they would like to see implemented. They are excited about it, believes it gets them a competitive advantage, and they have absolute confidence in your ability to get it done. The only danger is that, in order for it to do any good, it must be done in a month. Any later than that, and the window of opportunity has closed, and the whole thing has been for naught.

You look at their request, agree that it would be a valuable differentiator for them and agree that it’s entirely doable… but you also see that it’s more complicated than they are assuming, and that a month to get the whole thing turned around is ambitious to the point of being risky. Your gut reaction is, “If only they’d asked me this 2 months ago!”

And then your brain starts to churn… “How could we get this done in time?” “What would we need in order to shorten the timeline?” “Would we be able to split the work across more resources to get it done in that amount of time?” And then the doozy: “If we did X and Y, got help from so-and-so, maybe trimmed back the scope just a tad, and everything went 100% perfectly, I think we could pull it off…”

Danger, Will Robinson!

In my world of web development, this is usually where the wheels start to come off the wagon. The trouble is, the most common response is to try slapping them back on and getting back on the trail at full-speed.

Here are the things to remember when you hear the voices in your head trying to talk your gut into saying “yes.”

Nothing Complex Ever Goes 100% Perfectly
I’m sure there must be some type of work out there somewhere that can be counted on to go quickly. But it’s not anything in my universe. Whether it’s software development, change management, people management, process improvement or marketing campaigns, anytime you are dealing with the marriage of people, systems and processes, you are in a complex Bermuda Triangle of potential risk.

There are tons of things you can do to help manage that risk, mitigate it, buffer it and tap dance around it, but all of those things take time and resources. Underestimating the level of effort involved — or, worse yet, assuming it won’t be necessary at all — is like painting a big red bulls-eye on your project and then tempting fate to start taking pot-shots at your efforts.

Expectation Management is Everything
This one is a hard thing for people to remember, but it’s the truth: under-promising and over-delivering makes you credible, reliable and trust worthy. Over-promising and under-delivering unravels all of that — and destruction is always faster and easier than creation.  In other words: it could take you ages to build credibility, but only one misstep to destroy it. A plan that sounds good heading out of the gate, but falls flat before you hit the finish line does no one any good.

Worse yet, in an effort to accomplish the impossible, we often resort to heroic efforts. While that sound noble, it’s also short-sighted. Consider this: if you have a team that is working 20 hours per day to deliver, and even then can’t get it done in time to save the day, then not only have you burned your credibility with your client, but you’ve also burned out your team. If you are relying on heroic efforts to get things done, then you are setting yourself up for being seen as part of the problem, not part of the solution.

People do not like being told no. But, without fail, they’d rather know bad news early so they can plan for it, than to be led down a garden path with a lot of up-front “yeses!” only to discover they’ve ended up in a thicket of poison oak.

Yes Must be Unanimous
The scenario I’ve seen most in my career with startups is that the person who says “Yes!” to a client request is not the (only) person who is going to be needed in order to get it done. (Just about every single CEO I’ve ever worked for falls into this category.)  Before you tell your client “yes!” make sure that you get a “yes!” from all of the people needed to do the work. And make certain everyone is clear on what it will take.

One of the biggest complaints that developers have with project managers is that they are given top-down directions that include timelines they never agreed were realistic in the first place. This is not an unreasonable complaint. The flip-side of that, though, is that far too often, development teams don’t push back hard enough and actually say, “No, that is not realistic.” Instead, it’s too easy to say, “Ok” in a meeting, and then go back to their desk and grumble about it.

The best solution I’ve found to this problem is multi-step:

  1. Instead of saying yes to the client immediately, buy a little bit of research time and tell them you’ll get back to them once you know more.
  2. Meet with your team and — before telling them what the client’s deadline is — ask them how much time they believe it would take to do the work.
  3. Work through the details with the team a bit, so that everyone is comfortable that you are at least in the same ballpark with what you are expecting to deliver.
  4. Once you have a timeline that the team feels confident they can deliver, share the client’s deadline.
  5. Assuming the client’s deadline is sooner than the team’s expected delivery date, examine the delta. Are there things that could be trimmed out that would make it realistic to hit the deadline? Don’t try stacking a precarious house of cards in order to get to a qualified yes, but sometimes there are ways to whittle things down enough to make it doable.
  6. Step through a risk analysis excercise with the team.
  7. Identify multiple potential, realistic options that the entire team is confident in.
  8. Present several options to the client. Keeping in mind that not one of those options may be exactly what they originally asked for.

The bottom line: all business is about negotiation, and almost nothing is black and white. Be wary of looking at every request in over-simplified ‘yes/no’ terms. The answer to the client’s original request may truly be, “Oh, hell no!” But your response should (typically) be a set of potential compromises for them to chose from. Instead of ABC, it could be A within the deadline, with BC to follow shortly thereafter. Or it could be XYZ as a short-term fix, while ABC gets done in the background for next time.

Whatever the solution, a knee-jerk “yes” is usually the wrong answer if everyone’s gut is screaming “no!” — for both the reasons that Mike outlines in his post, as well as the reasons I’ve highlighted above.

Absolutely: be optimistic, be sensitive to new opportunities, be confident in your team, and be a valuable resource for your client. Just remember that you can’t do any of those things if aren’t realistic about the committments you make.

Alora Chistiakoff is an entrepreneur, content strategist and project manager who has been developing online business and technology for startups for more than a decade.  She co-owns The Indigo Heron Group, Inc., a content strategy firm in Austin, Texas

  • Allison

    Great post! I encounter these situations all too often as a project manager; I think a well-informed client is a happy client, and nobody wins when a simple ‘yes’ is said upfront and heroic efforts are needed later. An agile environment certainly helps, but it always comes back to regular, open communication with the client about what can and cannot be done.

  • Alora Chistiakoff

    Thanks, Allison. I couldn’t agree more. The client may be disappointed if you explain to them that their idea — while valuable — is unrealistic in a short amount of time, but no reasonable person is actually going to be ANGRY at you for it. But if you tell them you can do something, and then fail to hit their dead line, then you’ve just put them on an emotional and business roller coaster: you raise their hopes, just before dashing them to the ground. At that point, it’s not unreasonable of them to be angry at all. Business is often a deadline driven world, but it’s also a world in which there are an endless array of potential options. Just because you can’t build your client a rocket launcher in a week, doesn’t mean that you can’t find a scaled back version to meet their need some other way. The thing people often neglect to realize is that giving blanket “yes!” answers actually eliminates other, creative and potentially valuable options that have the potential of not only meeting the client’s need, but also instilling them with confidence in your ability to help them get where they need to go. Thanks for the comment! — Alora