One evening I was ruminating about management regrets.  We all have them.  Sometimes we learn… but too often we don’t.

I sent a flurry of emails to my CEO friends, asking, “Tell me about a time that when you made a CEO-decision that YOU KNEW DARN WELL you should have made much earlier but were nervous about…. but when you finally pulled the trigger EVERYTHING TURNED OUT JUST FINE.”

These friendly pillars of knowledge, offered these thoughts:

1. Going slow on investing just leads to wasted time as one ends up investing down the line anyways.  There is no investment better than investing back in a growing business.  Do your ROI analysis – if you won’t lose your shirt… go for it.
2. I’ve never regretted firing someone who wasn’t performing or the wrong fit, even after worrying about the decision for months.  On the other end of the spectrum, I’ve never regretted making a much-needed, but costly, new hire “too early.” In both cases, I always look back a few months later at my team say, “Why did I wait so long?”  JUST DO IT!
3. Getting nit-picky in deals and ending up not getting them done!  What a waste of time and loss of an opportunity – I was foolish!
4. Not hiring fast enough, thinking I can’t afford headcount, but not hiring is what I could not afford.  For example, It has been just about 30 days since our new VP joined, and he already has 15 multimillion deals in the pipeline with our existing partners.
5. Never wait to be tough in negotiations with bigger companies.   We were wrongfully being sued at the IP level by a big company because they were worried about us as a competitor.  They presented an irrelevant but related patent and sued us to try to scare us into selling to them.   Everybody around me was asking me to compromise and give up because it was just one of many market opportunities for us.  I refused to compromise.  We did the right thing and… extracted a very favorable settlement which gave what we needed in a very affordable way without having to go to the uncertainty of a trial (which the big player really didn’t want either).
6. Quoting customers list price for an upsell the customer asks for!   Salespeople are always nervous about offending the customer or losing a deal and I keep telling them there is nothing offensive about charging appropriately (never gouge!) for additional services.   I joined in on a call and it took me less time to get the customer to say yes to an additional element than it took me to get my salespeople to stop whining about being afraid to quote it.
7. Not saying “No” earlier in a deal/negotiation process whether it was for financing or revenue.  I’ve found its the fastest way to cut to the chase as to whether a real deal can be struck, but also nerve-wrecking at the same time.
8. Deciding to raise prices when the product value calls for it.  Sales guys never want to deliver bad news.  If we do our homework properly we usually get the expected result, but again, we’re always worried about irrational actors.  Stop worrying and do it!
9. Every time some one gets canned.  Everyone knows it for months but nobody has the “guts” to do it so I STEP IN AND FORCE IT.  Everything always comes out fine… actually, things get BETTER after the tumor is removed.
10. Overthinking, Micromanaging, Delaying, Denying, Hoping and then Dying.  You can’t layoff and cut expenses to get rich, you can’t hope your way out of a hole, you can’t micromanage your way to recovery.  You need dry powder in the form of capital so you can invest in the business and manage through the tough times.  This game is not for the feint of heart or the under-capitalized.