June 19, 2022

Delegation: Through the Looking Glass

Through the Looking Glass and What Alice Found There is Lewis Carroll's sequel to Alice's Adventures in Wonderland.  

In the story, she imagined there was a Looking Glass House that she saw "through the mirror." She wondered what life was like there and dreamt her way into it. There, she encountered the Red and White Queens again as well as new characters like Humpty Dumpty, Tweedledum and Tweedledee, and many others.  

Delegation is a great lens and a great mirror for leaders.  

It is a great lens because of the new insights it can provide about a team and the developmental opportunities that associates' day-to-day work performance might not be revealing.  

Delegation is also a great looking glass for leaders because it can reveal unconscious drivers, including judgments and fears, that are hard to see.  

What you can't delegate reveals important development needs for your team, which need to be included in their development plans if you are serious about helping your team level up.  

Delegation As a Lens: Deeper Insights About Your Team  

Leaders in well run organizations are evaluating the strengths and weaknesses of the people on their team all the time. They are making decisions about development strategies, pay increases, promotion readiness, etc at least every year and often more frequently.  

These annual assessments are typically about deliverables achieved and goals accomplished. In short they are about how members of the team are performing in their current jobs. Rarely is the feedback and development plan about improving the ability to deliver at the next level, that is, at the level of the leader doing the evaluating.  

How can you know about someone's ability to deliver at the next level?  


You get insights about a person's ability to deliver at your level by seeing how they do on what you delegate to them.  

More important, you can also get insights about their ability to deliver at your level by what you can't delegate to them. This is why delegation is such a good lens for looking at your team.  

If we assume your assessments are accurate (more on that in a moment), when you think about delegating your responsibilities to your team, what can't you take off your plate and give to, say, Maria? What would you not trust Vijit to run with yet?  

If you take nothing else from this article, take this:  what you can't delegate reveals important development needs for your team (as important as the skill/execution gaps around their current responsibilities), which need to be included in their development plans if you are serious about helping your team level up.  

Delegation: Rarely Enough  

I'll show my cards and say first, that I don't think leaders are delegating enough, which is depriving organizations of a higher rate of human development and an increased focus on more strategic and longer term outcomes throughout the company.  

Regarding the amount of delegation and with the leader as the "unit of analysis," my guess is most leaders think they are delegating plenty, but I would also guess their teams would disagree.  

Here are some acid tests for leaders about their delegation practices:  

  1. Have you delegated so much that your team regularly comes back to you asking you to re-prioritize their task lists because there is no way they will be able to complete them all within the needed time frames?
  2. Have you delegated so much that you actually go to bed worried about whether your team can handle all the work you have given them without something critical falling between the cracks?
  3. For the highest visibility at-bats with customers or upper management, how often do you allow members of your team drive all or at least some of the presentation?

In my experience, leaders who can answer "all the time" to all three questions are few and far between.  

Given delegation's ability to develop others and free up time to focus on the longer term and the more strategic, why aren't leaders doing it more?  

There are many potential reasons but two big ones are judgments and fears on the part of the leader.  

What's more interesting to me is what is going to be true a year from now. Will your team be able to handle a significant portion of what you are handling today in twelve months?  

Delegation As a Looking Glass (Part 1): Judgments  

When Alice dreamt her way into the Looking Glass room, the first thing she encountered was a fire blazing brightly in the fireplace.  

When you think about delegating more to the people on your team, the first thing you will probably run into is a blazing judgment of your own: You believe you handle the customer conversations, deliver the senior management presentations, do the analyses, run the meetings, etc better than anyone on your team can.  

Your assessment is likely not accurate because we all suffer from the Illusory Superiority bias, but, believe it or not, I am actually going to assume your judgment of their abilities is accurate and they aren't ready for you to delegate more to them.  

The reason I am not going to fight you on it is because a leader's current assessment of her/his team's ability to handle more delegation is not what interests me.  

What's more interesting to me is what is going to be true a year from now. Will your team be able to handle a significant portion of what you are handling today in twelve months?  

If you say "Yes, of course," then what is the sequence of skill building activities you're going to tee up to ensure that in a year's time your team will be handling more of the customer meetings, management presentations, analyses, and meeting facilitation? It is hard to imagine that you delegating more to your team is not the center pole of those capability building sequences.  

And while you are asking whether your team can handle your work and deciding why or why not, ask yourself if you are a leader mortgaging the future by prioritizing execution today over spending time building towards a preferred future. Because your orientation is going to play a much bigger role in where the team is a year from now than your team's current level of capability.  

Delegation As a Looking Glass (Part 2): Fears  

Even if you recognize you have not been delegating enough and resolve to delegate more, here is my prediction: a year from now, many of you will still think your teams are not ready to handle more, whether they are or not, and you will still be handling the work loads you are today.  

After noticing the brightly burning fire in the Looking Glass House, the next thing Alice noticed was that near the hearth of the fireplace the chess pieces were going two-by-two: the Red Queen and the Red King, the White Queen and the White King, even the two Castles were walking arm-in-arm.  

I guess that is always a risk. But for that to be true, you need an answer for why they would fire the gal or guy who developed the people on her/his team and got them playing at a higher level.  

Cost-cutting and eliminating layers does happen, but organizations are dying for "force multipliers." Maintainers of the status quo are a dime a dozen. If people can see what you have done with your team, in my view, it is as likely that they give you a bigger at-bat or another team to grow than it is that they get rid of you.  

A second arm-in-arm fear that clouds leaders' assessments of their teams' skills is a doubt about the leaders' skills/abilities to handle broader, less defined, higher-impact responsibilities themselves.  

The time you free up delegating "the known" and the tactical will need to be filled focusing more on the longer-term and the more strategic for your department/function, and/or on taking stuff off your boss' plate. The longer time horizons will mean more working in more ill-defined domains, and more work on your part to influence and align stakeholders around problems, opportunities and paths forward both at your current level and higher.  

Those new challenges are uncharted waters for many leaders and, like the old maps that pictured the world as flat with monsters right over the edge, can be downright scary.  

Fear of the unknown and doubts about one's abilities are uncomfortable in and of themselves. But those same fears also bias leaders' judgements of their teams' abilities to handle more.  

As a result, leaders stay in their comfort zones, decide their teams aren't ready and balk by continuing to immerse themselves in their current responsibilities.  As a result, they let the urgent/tactical/short-term drive out the critical/strategic/developmental long-term.  

Idealistic thinking that generosity and work on preferred futures can motivate us to get past our judgments and fears is, in my view, charmingly naive.  

The Path to Changing Delegation Behavior:  Rational Self-Interest  

It would be ideal if the opportunities to develop your team through delegation, which are legion, were motivation enough.  But judgments and fears often have a very tight grip on us and can be hard to get out from under.  

I have been studying behavior change for almost 50 years since I trained a mouse to press a bar for a reward in High School. Idealistic thinking that generosity and work on preferred futures can motivate us to get past our judgments and fears is, in my view, charmingly naive.  

Fans of Ayn Rand and her Atlas Shrugged and Objectivism, which, in part, advocate for a morality of rational self-interest, would argue a more promising path for increasing delegation is to get leaders to create an image of a preferred future...for themselves...and show them how more delegation can help them get there.  

And what is something almost every leader wants? They want to get promoted.  

I have never had a leader come to me and say, "I would like to pay you thousands of dollars to help me get better at my current job because I love it so much, I am hoping to do it forever."  

As the saying goes, "the best way to make Partner is to start acting like one." Delegation gets the tactical off your plate and frees up time to start "acting like a Partner" by focusing on more strategic, cross-functional, higher visibility efforts, improving your influence skills, and deepening stakeholder relationships, which are critical levers for increasing your power in the organization and for getting increased responsibilities and promotions.  

The question then about whether you are finally going to change your approach to what you delegate and the work you then free yourself to take on might come down to this: Hatred vs. Fear.  

Waking Up From the Dream  

But sometimes even self-interest isn't enough to change behavioSurely the fact that more delegation is good, not only for your team, but for you and your career can't be news.  

Like the articles about getting your 4000 steps in, spending less time on screens in general and social media in particular, increasing the amount of sleep you are getting, and eating more blueberries, you know what you should be doing.  But the truth is, it's not happening consistently.  

Speaking of truth, maybe you are not ready to delegate more, despite how it helps you and your team. Maybe you've thrown in the towel, shrugging your shoulders and giving your personality pejorative labels, such as "perfectionist" or "control freak."  

It is often said that shared values (or, sometimes, family/friends) are "the ties that bind." But in real life, fears are also the ties that bind. You might not be ready to push through your fears just yet.  

Try to take a deep breath of acceptance: We are where we are.  

As you start to accept that you are too afraid to take risks around delegation and next level responsibilities, you might also start worrying, "Will I ever be ready?"  

A question to which the only judicious response is, "That depends."  

The penultimate thing Alice said before she awakened from her Looking Glass dream, was "I can't stand this any longer."  Which was immediately followed by her yanking the tablecloth and sending all the plates, dishes, candles, and guests, including the Red Queen, flying.  

If you get tired of the status quo, tired of a team that is not progressing and gets the same performance review they got a year ago, tired of you doing the same work you have been doing for years, tired of being passed over for promotion, in short, when you, like Alice, "can't stand this any longer," then you might yank the cloth on that table set by none other than you, start taking some chances with what you delegate and what work you take on, and let the chips (and dishes) fall where they may.  

The question then about whether you are finally going to change your approach to what you delegate and the work you then free yourself to take on might come down to this: Hatred vs. Fear.  

Hatred...about the current, same-as-it-ever-was-lack-of-progress/promotion Vs. Fear...about some unknown, might-be-scary-what-if-I-stumble future.  

When it is Fear vs Logic (about what you should do for your career) or Idealism (what you should do for your team) the fight is between strong emotions and abstract ideas. Smart money is on the emotions.  

But Hatred vs Fear, with strong emotions on both sides?  In the realm of behavior change, now that's a fair fight.  

Go ask Alice.  

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