People Who Scale: Second Chances in Business

It can be worthwhile after an appropriate period of time has passed to reconsider one’s opinion of someone with which certain issues have been noted in the past. What should one get second chances for? How bad a deal breaker were the issues and in what context? These matters concern value judgment calls that outside of some broad strokes are difficult to generalize. Here we focus on the second chances relevant to business relationships. Any previous experience with the person should give areas of heightened scrutiny as you’ve seen their weaknesses before.

The generalized broad stroke analysis of suitable second chances in business are valuable to consider, since in business we must forge alliances, sign contracts, take and offer employment, and form other formal and informal associations wherein our character is bolstered or degraded by affiliation with another party. Here we limit the scope to the  category of prior issues and how the issue has changed with time.

Observing after hours conduct in potential colleague

Traditional networking takes place after hours, over drinks, perhaps with family. Sometimes cracks in the façade will show up already at this point. Particularly when giving someone a second chance, you should know what to look out for. Here are some key behaviors to watch out for that may have subtle manifestations, but if going in attuned, one might be more likely to pick up on.

  • Bullying
  • Demeaning attitude
  • Critical without balancing/qualifying with merits

Certainly more categories exist, but for brevity we consider these three.

On the lookout: Workplace Bullying

Bullying covers a wide range of behaviors and severity. Are their friends deferential, cowed, afraid or are they themselves also aggressive? Deference often comes from respect; does the person have the personality that elicits or demands respect (e.g. petulance)? Do you see markers of fear in their colleagues? Are their friends/colleagues bullies? Extortion and other Machiavellian behaviors toward subordinates can actually look good to their superiors. The person is reinforced by feeling they really extract the maximum value out of every person and deal. In any field, contractors are numerous, so squeezing the blood out of each one until they are used up can seem to be smart/savvy business.

One of the enabling qualities of a bully is a certain functional level of sociopathy. You can sometimes get strong hints of this at gatherings where their family is present–do they treat their loved ones with respect or as functional annoyances. Of course at pure business gatherings, one can rely on the non-verbal cues to see how they react to people, particularly those at different stations in the business. Do they treat service workers with respect or with undertones of nasty comments? These are little peeks into what you might soon be feeling full force in your employment, co-founder, or consulting agreement with them.

If the person is an old school buddy, you will have an even greater sense of what to look out for from former social interactions. Allowing for cultural changes and personal growth that may have happened since then, nonetheless, recalling how they behaved under the pressures of undergrad or biz/grad school will let you focus your attention to these areas. Maybe you can even raise a trial balloon, seeing how they feel about some issues that isn’t obvious like national politics. How do they approach the “bait”? If you’ve known them for longer and family comes up, what is their attitude toward struggles in the family?

On the lookout: Demeaning attitudes in the workplace

If you get a bite so to speak, is the undesirable expression due to lack of information/education, or is it from a baseline hatred of other people? Is it driven by gender or other prejudicial bases? Do they make inappropriate gender-demeaning comments, do they do that in front of their significant other? (especially if the S.O. is of the demeaned gender!) This could be a harbinger of a broad spectrum of negative personal traits that could make your potential business relationship undesirable.

There are a spectrum of services that will scrub social media and search results for someone suffering from prior indiscretions. Even legal trouble can be covered up from the casual searcher. Catch someone at cocktail hour and things can come spilling out that can be warning signs of what may come at more sober hours. If someone will demean someone else based on gender, appearance, physical characteristics, etc. how much more will they demean and attack when there is an advantage to them appearing the savvy businessperson dealing with an apparently incompetent employee/contractor/partner. We shouldn’t make too many excuses for them, especially when they’re a company executive. We have seen some widespread reputation damage to the company and career/personal damage to numerous victims when an early-stage executive is allowed to run free due to superiors’ lack of perception of the problem.

On the lookout: Unbalanced Workplace Criticism

The unbalanced criticizer, who may soon be criticizing you, does not have the ability to handle cognitive dissonance or have the empathy to see the other side of an issue they feel casually or passionately about. We see enough of this manifest in national politics, and one easy test of this negative characteristic is to mention competitor products or other things you suspect they oppose. If hyperbolic bluster comes out, perceive that the winds may be aimed at you for the first sign of difficulty, even without fault from you.

You should realize that someone with the negative traits in this article will not understand ill children that need care (come in on Sunday and make it up.) Kid hospitalized? You should have been working extra already in case that happened. Kind of like reverse sick time. There are many tricks that can be played in the workplace for which there is little protection within or outside of the organization. One must constantly network and even take an interview now and then to be ready to escape a situation before it spirals. If a contractor, don’t allow yourself to become a one-client wonder.


You must always look beyond the paper accomplishments and popularity/pizzazz of one with whom you’ll do business as a colleague, co-founder, or consultant. Within legal and ethical bounds, it pays to lookout and probe the person outside the professional scene to look for these traits bubbling out. We aren’t looking necessarily for awkwardness in and of itself, but rather uncovering prejudices, unwarranted or medieval attitudes and Machiavellian character traits. You might well find yourself in a place where 3x the income wouldn’t make it worth it. Your and your family’s health and well-being can be impacted. Before taking on a job or position with someone you’ve met for the first time and especially if someone you’re giving a second chance, dig beneath the surface. If you’ve already gotten in, take the escape valve you must always leave yourself. You can’t teach them anything their family and friends haven’t already. You might be better off without the deal of the century if you’re risking your own personal ethics and image by being associated with a bigot, bully, or half-baked personality surrounded by enablers–one of which you might well become.

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