Avoid Bad Apples in Business Transformation

Doug Wilson
4 min readJan 15, 2022

By getting them off the tree rather than going to the barrel

Photo by cottonbro on Pexels.com

In the 1987 Brian De Palma film The Untouchables, Eliot Ness (Kevin Costner) faces an apparently insurmountable challenge. Al Capone (Robert De Niro) and his organized crime family have Prohibition-era Chicago in their violent, corrupt grip, and it seems that everyone else is either on the take or intimidated and relegated to the sidelines. City politicians, judges, and even the police are on Capone’s payroll.

No one believes that bringing Capone to justice (or at least accountability) is even possible, given the level of corruption … except for Jim Malone (Sean Connery), a tired, old beat cop who doles out his hard-won street wisdom in a thick Irish brogue. In order to avoid corruption in Ness’s own team, Malone advises him:

“If you’re afraid of getting a rotten apple, don’t go to the barrel. Get it off the tree.”

Solving deeply entrenched problems in large organizations can sometimes feel the same way (without the guns, violence, and pinstripes). What’s at stake? Who to trust? Where to start?

In the film, Malone’s “tree” is the the police academy — the source of new, as-yet uncorrupted cadets — uncorrupted but not unskilled, a point often lost on the casual viewer. To the close observer, three other, vitally important characteristics are clearly also being sought:

  1. The ability to shoot well. Ness and Malone understand all too well that their crusade to rid Chicago of Capone is likely to involve exchanges of gunfire; therefore, Malone requests the two candidates who are consistently the best shots.
  2. Self-awareness and the ability to think clearly. The first candidate disqualifies himself by stammering and struggling through his reason for joining the police force.
  3. Passionate courage. Malone tests Giuseppe Petri aka “George Stone” (Andy Garcia) by provoking him with racial slurs, but Stone stands his ground and gives as well as he gets. Not advocating racial slurs. This is a movie. About Chicago in the 1920s.

Bad apples in the film’s police force were corrupt cops, but in the context of necessary organizational change, they can be anyone who is satisfied with or bought into the status quo. Team members who don’t understand the need for change (neutral stance) or who actually oppose it will greatly increase the time and effort required and may cause the initiative to fail altogether.

If you decide to avoid bad apples by getting them off the tree, have a clear idea of the skills that will be crucial to the success of your initiative — the skills they’ll need to already have developed — and evaluate candidates in terms of these skills. Sales, strategic planning, tactical implementation, project management, technical design, marketing, operations, analytics, etc are skills that take years to develop and even longer to master to the point where a candidate is consistently at the top of her/his class. Your initiative doesn’t have time for candidates to develop or refine these skills. You need ripe apples, ready to rock, not promising or enthusiastic blossoms or seedlings. Look for relevant experience and lots of it.

Effective candidates are confident, know themselves, and can (and consistently do) express their thoughts, needs, status, etc. Dialog is one way to gain insight into a candidate’s ability to think clearly. Diagramming is another. Thinking through a problem together visually as well as verbally is a great way to discover not only whether the candidate thinks clearly but also to get an indication of probable compatibility. Does s/he approach and solve problems like you would (or in a complementary fashion)? What can you learn from her/his approach? Does it aggravate or inspire you?

Personalities and the disagreement and conflict they can engender are part of any project, but transformation projects involve a lot of change, which people generally hate and fear. This can raise stress levels across the board, including inside your team. Saying “yes” (or remaining silent) while having serious reservations in order to avoid confrontation or conflict is as dangerously corrosive a behavior as constant criticism and complaining. Team members need to be willing to be persuaded, but they must have the courage to stand up and say no when necessary.

Finally, as useful and entertaining as The Untouchables may be as an unintended source of 21st-century business transformation wisdom, please avoid the temptation to frame your struggle in terms of absolute good and evil. Capone’s organization blew up little girls. That’s real evil.

“Here endeth the lesson.” — Malone

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Doug Wilson

Doug Wilson is an experienced software application architect, music lover, problem solver, former film/video editor, philologist, and father of four.