What happens when board behavior doesn't go exactly as planned?  "Hacking your board" helps early start-ups deal with a board and make the best of a situation they cannot fully design or control. There are hacks for planning and running meetings, along with a checklist of expectations you should have for your board.

Even assuming your directors understand their role broadly, there can still be significant issues to contend with. These fall into four broad categories: issues with logistics, attitude problems, interpersonal problems and competence deficits. We've looked at some key issues with director roles and logistics behavior, and now lets look at attitude problems, with interpersonal problems and competence deficits to follow.

Director Attitude Problems

Being in a start-up is a bit like riding a roller coaster. There are times when you are up, and there are times when you are down. Regardless of whether you are up or down, there is almost always uncertainty about the right direction forward. It can be stressful for all involved. Having one or more directors with the wrong attitude in your board room can be a tremendous challenge and drag on your effectiveness.

Attitude problems fall into three broad categories: excessive optimism, excessive pessimism and outright cynicism.

The Cheerleader

The excessively optimistic cheerleader never has feedback, never pushes back, loves everything proposed, thinks every plan is achievable, and thinks hope is a strategy. Not only is this laziness a waste of a valuable board seat, if it is associated with a dominant voice in the room, it can make it that much harder for other directors to contradict and offer you the advice and ask the questions you need to hear. It can cause a shallowness of board room analysis and create momentum towards a rubber-stamping mentality.

Dealing with it can take some self-awareness and a deft touch. Self-awareness because everybody loves flattery and support. Confirmation bias can make it hard to recognize when you are just grabbing at what you want to hear. It is hard not to think the person who agrees with you is the smartest person in the room.

But you need to challenge yourself to recognize superficial input from a cheerleader and push them to go farther. Ask them why they like it. Ask why they aren't worried about this or that aspect. Ask them to expand on their thinking or to reconcile their view with that of the others in the room. Drawing a cheerleader out can often force them to go a little deeper and give you the more nuanced advice you need.

The Pessimist

We have all seen them. This person is not merely having a bad day. This is the person with a permanently sour outlook on life. The pessimist hates every idea, thinks everything proposed is doomed to failure, says "I told you so" to every setback, and always thinks the resources are too scarce or the time line too long, or the effort not worth undertaking.

Pessimists can not only be terribly annoying and a real buzz-kill, they can drive the ambition out of a plan and lead companies to embrace overly-modest and "safe" strategies that doom them to mediocrity. They sap energy and drain enthusiasm. Dealing with them is not always easy. Sometimes it is possible to jolly them out of it by giving it a label or a nickname: "Steve, you are doing your 'grumpy cat' impression again?"

As with cheerleaders, it can also work to draw pessimists out: "you seem overly down on this plan; what is your main concern?" Or, "I understand there are risks here, but don't you think we have taken adequate steps to address them?" "Others have expressed enthusiasm - help me reconcile?" And, as with cheerleaders, you can enlist other directors in the effort to manage pessimists: "Sarah, what is your reaction to Steve's concern?" "Bob, what do you think about Steve's question?"

Another technique can be to ask them if they can suggest any modifications to the plan or any alternatives to the plan that might improve it. In that vein, asking whether some kind of a test would be their preference. If you are going to go down that path, seek out clarification regarding what milestones or interim data would they need to see to get them comfortable with the proposed approach.

The Cynic

The cynic may be the most troublesome. They take skepticism, which is about attacking the underlying facts and assumptions of an assertion, much further. A little skepticism can be a healthy part of any constructive debate, provided it is not chronic enough to fall into the pessimism category. Cynicism is not attacking the premise of the assertion, but rather is attacking the motivations and character of the person making them. Cynicism is extraordinarily destructive in the boardroom. It really cannot be tolerated, even briefly, and should be called out and dealt with immediately.

It's great to have skeptics who challenge you to do your best thinking, but it is death to have a cynic who is questioning your motives or character. If a director is approaching every discussion with the assumption that you are not telling the truth, or cannot be trusted, or have an agenda that differs from the directors, you need to go have a sit-down with him/her and sort it out. This director either needs to become comfortable with your motivations and character or  needs to leave your board. There is no way a board can function effectively if one or more members is starting with the cynical premise that the CEO is misleading the board. It is a caustic dynamic that will break down the trust of all involved and entirely preclude any effective operation of the board.

Hopefully with some deft handling, you can use the above advice to deal with the cheerleader, the pessimist and the cynic. Next up we will look at dealing with the interpersonal problems and competence deficits.