Anatomy of Ineffective leaders

Five tell-tale signs of poor leadership: from speculating on stocks to making bad offers. Patterns observed over 10 years that consistently predict worse company performance.

Over 10 years of being someone's worker, leaders that own those characters demonstrate worse track records in company performance than leaders that don't have those characteristics.

1/ Speculating on stocks or futures

A leader should spend all their time creating and engineering a better future. Speculating on markets outside their expertise should be a waste of time if they really know what they are doing.

Even lower confidence if I peeked at their portfolio and notice them losing trades on speculative assets. Is that the reason why my boss urgently needs money and productivity?

There are some exceptions, where a great investor is also doing the hands-on work of running a company. 1

> be leader/CEO
> supposed to focus on vision and product
> spend mornings checking stock tickers
> "guys, need all hands on deck" after losing money on Tesla calls
> can't explain what a covered call even is
> betting company money on crypto, meme stocks, and 10x leveraged ETFs
> mood swings correlated with S&P 500
> "we need to push for more revenue" (portfolio down bad)
> wonder why employees don't trust direction

2/ Threatens misbehaving employees with pay cut and termination

If an employee is a problem and you can do without them, terminate. Don't need to threaten.

If you must threaten, intimidation is a poor strategy to motivate someone who is underperforming or misbehaving -- a leader that makes a poor strategy is a poor leader.

What happens when you threaten is resentment and people preparing to jump ship as soon as they find the opportunity. Bad retention strategy.

Roll for persuasion, not intimidation.

> be boss
> "If you mess up again, I’ll cut your pay and fire you!"
> think threats make people work harder
> wonder why everyone updates their LinkedIn the next day
> "Why is morale so low?"
> top employees already talking to recruiters
> team only does the bare minimum, waiting to bail
> retention rate drops, company reputation in shambles
> MFW "Why does nobody want to work here?"

3/ Not respectful of other people's time

By showing up late, or keeping people overtime on projects or meetings.

Usually, this behavior is confounded with regular poor business judgment.

They tend to have budget issues and lack of manpower issues, but I hypothesize the true cause is that they cannot properly allocate priorities.

> be boss
> always late to meetings
> expects the team to stay late to fix "urgent" mistakes
> Zoom calls drag on forever, nothing actually gets decided
> "Let's squeeze in one more thing before we wrap up"
> doesn't notice when people are burnt out or missing family events
> thinks time is an infinite resource (as long as it's yours, not theirs)
> TFW I wonder why deadlines keep slipping and nobody volunteers for extra work

4/ Underpays or too much cost-cutting

You don't build a sports team that wins by buying players at wholesale prices. Lots of people do it, but I haven't seen one that works.

If someone really had a good solution to your problem, you pay as much as you can to get it.

Underpaying and cost-cutting is also a behavior that's confounded with priority issues similar to (3).

Underpaying, while it works against workers who are desperate enough to put up with those conditions, also has the effect of hiding the real costs of the problem.

Leaders will take for granted that this is all the investment that needs to get things done (at unsustainable prices) and think they have margins to pursue even worse market ideas.

You don't win from someone's losses by lowballing. You also lose out on real information that would have stopped you from pursuing bad ideas.

> be boss
> expect world-class results but pay minimum wage
> team is always leaving for better offers elsewhere
> "I don't get why nobody is loyal anymore"
> hire cheapest contractors who barely speak the same language
> project delayed, quality is rock bottom
> spend more time fixing mistakes than making progress
> get shocked Pikachu face when star employee quits for a competitor
> "Why is turnover so high? Why are our best ideas failing?"
> TFW penny pinching always costs more in the end

5/ Bad offers

The best signal starts from a good offer. A shitty offer either means the founder:

  • didn't do his market research
  • sucks at marketing 2
  • cares more about himself than you or the mission
  • thinks he can get away with cutting corners and regularly practices it
  • rather wins the battle and loses the war

In 10 years of my working life, I have never seen a founder making bad offers to not have any of these problems. 3

> be startup founder
> sends intern a job offer at 50% market rate
> nahhh_man.jpg
> "but there's huge upside and plenty of equity"
> equity = 0.001% in an LLC, fully diluted, 10-year vesting cliff
> "You'll learn so much and be part of something special"
> tries to guilt intern for negotiating for market salary
> nahhh_man.jpg
> "If you really cared, you'd take this chance"
> same guy spends $30k on a rebrand, $2k on swag, $4k for blowjobs and OF videos
> LMFAO can't raise, can't recruit, blames market conditions
> TFW intern walks away and founder company folds in 18 months

Footnotes

  1. In rare cases, I met leaders who are great investors and they are great people to work with as they understand macro, accounting, and good business models. I hold suspicion to leaders who are responsible for a large part of the company and its workers future, but somehow find time for short-term derivatives and engage with trading systems they cannot explain.

  2. If he sucks at selling the role to you, he will suck at selling the product to the market.

  3. That said, its important not to feel entitled to what offer he should have. Being a founder is tough. There are many cases where I offer my partners more than what I would get and still get laughed off (rationally or irrationally). I just treat it as me not capable enough and take it as a signal to go back working on the small things well before going after the bigger things again.