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Struggle to delegate? Three behaviors to watch out for

My first job out of undergrad was on the Lehman Brothers interest rate sales desk. I sat on a trading floor amongst some of the best financial professionals who transacted multi-million dollar deals on a daily basis. The work was incredibly stressful and required a tremendous amount of attention to detail and accuracy. If you made a mistake, it typically cost at least $50,000. I worked in a team consisting of 3 senior salesmen, an associate with three years of experience and myself – a clueless college grad. At first, no one trusted me to do much of anything except get coffee and make copies. Over time, I began to take on more client facing responsibilities (writing trade confirms, answering phones and writing market commentary). Executing one of those multi-million dollar trades was off limits though. I didn’t have the skills yet, and no one was interested in losing money due to my lack of experience.

As weeks went by, I wondered when I would get my chance to show everyone that I was ready to step up and execute trades. I was getting antsy to take on more.

And then it happened! My associate went on vacation, and I was up to bat. My security blanket was gone, and the senior salesmen had no choice but to throw me into the fire.

I can write a book just about that week; the week that everything was new and terrifying. That was the week that I showed the team I was capable of a lot more than they thought. I learned more in that one week than I had in the two months prior and I became a more valuable resource to the team. Being thrown into the fire was the best thing that could have happened to me at that point.

Think back to your professional journey and noticed that your greatest growth moments are when more experienced team members are away, you did work you never did before and you had no choice but to step up.

We know that we grow the most when given a chance to be challenged.  We frequently crave more responsibility from our managers.  Why then, when we are in the leadership role, is it so difficult to delegate effectively?

Delegation is one of the most challenging leadership skills to master not because it is a complex skill but because a lack of trust acts as a major roadblock.

So, if you want to delegate better, you need to trust more. Easier said than done right? Trusting and delegating is a bit of a chicken or egg scenario. If you don’t trust you won’t delegate, but if you don’t delegate you can’t develop the trust.

Here are three things you should watch out for if you struggle with delegation.

Half delegating/micro-management

You might find yourself “half-delegating” if you assign work and then check everything before it is sent out to clients/managers/others. A recent study in the Journal of Experimental Psychology showed that people who believe they are being watched perform at a lower level. Half delegating and micromanagement eventually leads people to feel disengaged from their jobs, reduces their motivation, and ultimately decreasing their performance.


Testing is when you provide a lot less information about the assignment/project than you would typically and add no support. You are setting this person up to fail. The only thing this accomplishes is that you support your theory that you shouldn’t trust this person but what you fail to realize is that you sabotaged them from the start.

Lack of social awareness

As a manager, it is your job to know what your direct reports’ strengths are and where they are weak. If you don’t bother obtaining this information, you won’t be able to assess if your assignment is appropriate for this person thus yet again setting them up for failure.

Remember to think back to those pivot moments in your career where a situation or a trusting manager gave you a chance to prove yourself. Empowering your team through delegation has a huge payoff for you in the long run!

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