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When something doesn’t feel right, it probably isn’t.

Hindsight is easy. When I make a decision I regret, I’ve noticed that it’s easy to see where it went wrong if I’m looking into the rearview mirror. What I’ve learned is to be kinder to myself when this happens because being objective in the moment isn’t something we’re going to get right 100% of the time. Mostly because of the breakneck speed of business these days. And also because we’re in a startup team that operates on very limited resources and very few people so our competitive relevance depends on speed to market. But I don’t let myself off the hook entirely though either. Being agile, also means learning from experiences that go south and finding quick heuristics to help one be more objective the next time around. I’ve found four hacks that can help: 

1. Ask other key team members for their point of view before you pull the trigger.
Ask them for absolute honesty though, because sometimes they just go along with you because you are the leader or because they think you know more about the situation. Hindsight is going to be easier for them too and they will throw the blame to you later. So ask for radical honesty anyway and they may give you something to chew on. 

2. Date before you get engaged.
I’ve learned that making business decisions is a lot like dating. Whether it’s a partnership, a new vendor, a new hire or anything involving humans, chemistry matters. Compatibility matters. Alignment is essential. But it takes time passing to tune into these perspectives. Business also has honeymoon periods so start with temporary arrangements and graduate the commitments over time. In early relationships everyone is on their best behavior and have not figured out if they can disagree or process conflict honestly yet. They may also simply have work habits that drive you nuts. It’s okay to have preferences in your team culture. Not everyone is going to fit with the specific crazy way your team does things. 

3. Trust your gut and don’t second-guess it.
Our primal instincts for survival are honed over many more years than our more human conscious thoughts. And they are 70,000 times faster. If your inner gut is telling you something is amiss, it is more often right than wrong. It doesn’t mean the other person is a bad choice for everyone, it just means they are wrong for YOU or your culture. A poor fit. And you, as leader, must consider the negative impact one person can make on the team climate. We can’t put the good of the one before the good of the many. Even yours, as leader.

4. Communicate specifics a lot. Especially in the dating agreements.
Then later in the engagement agreements. Be as specific, objective and clear about concrete deliverables and expectations on both sides and make sure it’s balanced. Then write it down in a simple agreement and sign it on both sides. Also add a clause that if a misunderstanding happens, it will be handled by a specific mediator who will facilitate an agreement for moving forward. Whatever you do, don’t get lawyers involved until you get married. Even then it can be the demise of the partnership because lawyers are best at seeing one side of an agreement and can polarize people into extreme corners instead of helping you find a way to negotiate a win-win, which is the only arrangement that is actually sustainable. 

I’ve learned the hard way that these four precautions will remove most of the risks that can result from what others will label later as “your impulsive decisions”. My two cents is that we have to go fast to lead today, so we have to wage some level of risk and take the heat if things go sour anyway. If we follow these simple steps, then we did what we could without sacrificing speed. Remind others who might say “I told you so” that they should have been more assertive if they say they saw issues and didn’t tell you. The next time they might choose to be more forthcoming with what their gut is telling them too, increasing our odds just a bit more and saving precious lost energy that is spent on fixing problems after they happen. 

Being objective requires us to step back and notice first, give it a whirl, and leave ourselves an out if things go awry anyway. It’s all part of being agile. Move on.