There is a surprising amount of talk about digital transformation as if it happens every day. The opposite is closer to the truth.

Digital transformation is only happening because it's too late and it was forced on the company by outside investors or new management due to years of neglect, changing consumers, or rising competition.

Like the frog slowly boiled in water (who tried this btw??), external forces happen slowly, and then all at once. This forces me to think about how companies make decisions.

These forces are often exacerbated by the HIPPO effect. The HIPPO effect is the embarrassing truth of many major corporations: "Highest Paid Person's Opinion." If the HIPPO doesn't want to move, then the entire corporation may not move.

A surprising amount of decisions come down to the "comfort level" of the HIPPO.

The truth in any major decision-making process, younger employees are not in the room -- they are lobbying up towards often ineffective middle management.

Mid-career employees know it's not their turn to rock the boat. And besides, they never get all the information, anyway.

The highest paid person is often not going to setup a meritocracy because they got their job because they were friends with the CEO. And will they defer the decision to a change committee or newly hired up-and-coming leader?

Not when their job is on the line.

Organizations like this have no real cross-department collaboration or teamwork, either. Communication only happens with missiles sent between VPs and SVPs up and down the chain.

Can true transformation happen in such an organization?

Sadly, the answer is no. This has a not-too-surprising effect on talented employees: fleeing. Smart software salespeople - particularly in high-ticket deals, should likely flee these situations well.

The best way to judge is to compare these organizations to your top existing customers: quality of employees and quality of decision-making processes: if neither are present, better to come back when an opportunity presents itself.

Until then, keep up relationships but don't overinvest in a losing proposition.