The Art and Skill of Delegation

By Steven Cerri

Delegate, delegate, delegate; this word is often heard by new managers as a important key to their success.  Trainers and books claim that one of the duties of a new manager, of all managers for that matter, is to delegate, and they will quickly give instruction on the skills necessary for successful delegation.  Delegation is often seen as assigning tasks to people and letting them have the personal and professional freedom to accomplish the tasks their way, and this is often called empowerment.  If the employee succeeds then the manager applauds them and if the employee fails the manager gives them 'constructive criticism’.  I think this is a completely ineffective strategy for delegation. 

Whatever the books and trainers say, to the person doing the delegating, the manager, it never seems quite so simple.  Even to the seasoned manager, delegation seems more an art than a skill.  So what is it with this delegation stuff?  How should we delegate?  What is delegation all about and how should you go about it?

Delegation has two major components; the first component is comprised of the skills of delegating and monitoring of tasks.  The second component is the relationship between the person delegating, the manager, and the person who is being delegated to, the employee. The first component, the skills, comprises the easy part.  The challenging and seldom taught part is establishing the relationship between the manager and the employee so that the delegation process will work.  This paper is devoted to establishing the relationship so the delegation process will work.  The next reasonable question is ‘How do you establish the relationship so that the delegation process is successful’?

To answer this question, first let’s take a look at what delegation requires.  However, you look it, delegation is about trust.  In order to delegate successfully to someone a certain amount of trust is required.  The level of trust the manager has for the employee dictates the type of project assigned and the processes that are used to monitor the task or project as it continues along.  If the level of trust is very high, it is likely that the manager will not monitor the project nearly so closely as would be the case if the trust the manager has for the employee is low.  Therefore, you can see that trust is a determining factor in the level of monitoring conducted by the manager or the “freedom” to be exercised by the employee.

So, what builds trust?  If trust is a critical ingredient to the delegation process, lets start by asking the question, ‘What causes trust to either exist or be absent in the relationship between the manager and the employee’?   ‘How is trust developed between a manager and an employee’?

The answer to this fundamental question is not simple in implementation but is simple in explanation.  Trust, as I am using it here in the business context, is defined as the perception that someone thinks like you.  It is that simple.  In order to trust someone, you either believe that they can get the job done or that they will go through all the processes that you would go through to get it done, and the closer their processes of thinking and doing are to yours the more you trust them.  Even if you believe an employee can get the job done but they go through thought processes that are significantly different and more disruptive than yours, you still won’t trust that employee.  Therefore, no matter what the arguments or situations might be, it all boils down to the fact that we trust people who think like us.  It appears to be a natural tendency of human psychology.  As a manager, when we have people working for us, we instinctively and intuitively trust people who we perceive as thinking as we do.

Now the mistake made by many managers is that they let this process happen haphazardly. My question is ‘Why not control it’?  That is, why not consciously train people to think like you?  As a manager, you evaluate people on this ability anyway, so why not train them to do it from the start?  When a manager conducts a performance appraisal, what are they evaluating people on?  If you are a manager, you have already “bought into” the culture and philosophy of the organization.  Someone that receives a high-performance appraisal from you, by definition, is doing the same thing.  They are thinking and acting like you and by extension like the organization.  This applies for both the well-structured, bureaucratic organization as well as the entrepreneurial start-up. 

The usual answer given to why managers do not consciously control this process is that it sounds too egotistical, too self-serving.  But that’s not really fair.  If we are evaluating people on our level of trust with them anyway and on a subconscious level we are evaluating them closely as to if they think as we do, why not train them in these requirements at the start?  It is a much more effective and honest way to conduct ourselves. So how do we do this?

First, as a manager, or a new manager, you know there are people you instinctively trust from the beginning.  I'll call this Group #1. There are others that you learn to trust over time, Group #2. And there are those that it seems you will never learn to trust no matter how much time you are given, Group #3. 

The ideal situation would be that your team is made up of people in Group #1, those people that you learn to trust quickly because you can tell they think like you. 

There will also be employees in Group #2, such that, as time continues, trust grows. Slowly, you learn that they think like you and that they cover all the “bases” that you would when they approach a task.

And, unfortunately, there are those employees in Group #3, such that no matter how much time you work with them you just never quite get to the point where you see that they think like you.

Of course, we now understand that the reason you trust a person is that you perceive that person thinks like you.  This is not such an odd perception.  How else do we recognize that we can trust people except that they go through the same thought processes as we?  How do we decide that we like someone except that we recognize that there is something very much like us in them.

Some people will automatically think like you from the beginning.  These are the people we say that we just “click” with.  There are others, the majority, who don’t think like us and so the next question is “How do you get someone to think like you?”  The best way is just to tell them that that is what you want from them. 

When I have new employees working in my group, after two weeks of working together and getting a sense of who they are, I tell them the following: “I’m going to apologize right up front for what I’m about to tell you but I don’t think there is a better way to do this.  If you want to advance with me, I have to be able to trust you.  The only way, I think that people learn to trust other people is that they perceive that the other person thinks like them. Therefore, if you want to gain my trust you will have to, at the very least, show me that you think like me.  I will want you to ultimately think beyond me but as a foundation you will have to think like me. What that means is that I don’t want you to come to me with a problem or an issue without at least two possible solutions that you think will work.   This is important because if I don’t have a solution that is better, we are going to go with one of yours.  So, make sure you come with at least two viable solutions.  Next, I’m going to ask you a lot of questions when you come to me with a problem or issue and your possible solutions.  I don’t want you to tell me, ‘Well I’ll have to go away and get the answer to that and get back to you.’  If you want to show me that you can think like me, come to me already having thought of all the questions I could ask and have the answers ready.  From my side, I’ll make sure that I ‘think’ out loud so that you begin to understand my thought processes and begin to understand what I expect.”

Now let’s unpack the above paragraph.  I will analyze and explain each sentence.  In doing so I will explain the reason for the statement and what I expect to achieve by making this pronouncement to the employee.  Also, it is important to note that I make this statement, in this form or in an abbreviated form, to all my employees regardless of their experience, and I repeat it in various verbal forms and behavioral forms for most of the time they work for me.  This message is a constant representation of our relationship and of my expectations.  So let me explain.

 “I’m going to apologize right up front for what I’m about to tell you but I don’t think there is a better way to do this?”  It is true.  What I’m about to say to the employee is worthy of an apology.  It does sound egotistical.  It does sound self-centered.  And yet there isn’t a better way.  Since we evaluate people and establish our trust of them on how closely they come to thinking like us, and most managers do this unconsciously, I think it is much better to be open and honest about this.  It takes courage on the part of the manger, and it takes an apology to set the stage for what is to follow.

“If you want to advance with me, I have to be able to trust you.”  This is another true statement.  The only way people advance in a business organization is that management perceives that the employee can be trusted to think like management wants them to think and that the employee accomplishes what management wants accomplished.  Well, before management will trust that an employee will accomplish what management wants, they must first be trusted to think like management or management won’t even give the employee the opportunity TO Do what management wants done.

“The only way I think that people learn to trust other people is that they perceive that the other person thinks like them.”  This is a very interesting statement when it is first heard.  It is a statement of human fact.  100% of the time when I say this to someone there is an instant of time when they are analyzing the implications of this statement and they are not quite willing to accept it.  But invariably within 5 to 10 seconds, the expression on their faces changes to one of complete understanding and acceptance.  After understanding this statement, it becomes completely intuitive that as human beings we don’t have any other way to trust someone.  Even if another person gets a job done but does so in a way that does not match with our thought processes, our values and beliefs, we will still not trust them.  We might trust them to get the job done but we will not trust them completely because their processes might be too disruptive or different from our processes. Trust is about perceiving that the other person will go through the same “processes” as we would, that is, the same thinking processes expressing the same values and beliefs.

“Therefore, if you want to gain my trust you will have to, at the very least, show me that you think like me.”  In this statement, the employee is being told exactly what they have to do to get ahead.  Finally someone is being honest with them.  Most people in organizations do not fail because they don’t get the job done, they fail because they do not “fit”.  The above statement is about “fit”.  It is a clear direction as to how to “fit” and ultimately how to be trusted enough to be delegated to and how to advance in the organization, my organization.  Now the individual does not have to agree or accept this directive.  There have been plenty of managers I’ve worked for who’s’ thought processes were completely uncomfortable to me.  And even though they didn’t make this statement, I understood better than they did that they would be grading me on whether my thought processes were similar or dissimilar to theirs.  And guess what, I didn’t fit and I ultimately left their organization.  The beauty of this statement is that it puts everything on the table and allows the employee to choose the path they want to take consciously.

“I will want you to ultimately think beyond me but as a foundation, a first step, you will have to think like me.”  This statement expands the concept somewhat.  The goal is not to end up with a bunch of clones.  You don’t want a team made up of people who ONLY think like you.  You ultimately want people to expand beyond your own thinking processes.  You want people to bring in their own gifts.  All you are saying here is that first, in order to trust enough to delegate to them, they must, AS A MINIMUM, provide a thinking process which covers what you would cover in your own thinking process.  Second, you would ultimately like them to think even beyond that.

“What that means is that I don’t want you to come to me with a problem or an issue without at least two possible solutions that you think will work.”    This part of the statement is where I now transition away from philosophy and move to concrete, unambiguous behaviors.  It is important as a manager to always provide the two components of delegation; 1) establish a philosophical foundation supporting the ‘why’ of what you want done; and 2) clearly define the actual behavior you want performed.  In the above sentence I am describing exactly what I want in the way of behavior, I am asking for two solutions from the employee for every problem they bring to me.  This forces the employee to begin to view me not so much as a parental figure to whom they should bring their daily problems, but rather a wise teacher to whom they are to show that they are capable of solving the problems on their own.  This is the beginning of the training process to make the employee self-sufficient and you, the manager, must stick to this structure.  Most employees who have worked for me are fond of telling my new hires; ‘Don’t bring any problems to Steven without a couple of good solutions because he’ll just send you on your way again until you have them.’  That’s a reputation worth developing because it means you have an environment where you will grow your people to excel and ultimately excel without you, which is a good managers’ ultimate goal.

“This is important because if I don’t have a solution that is better we are going to go with one of yours.”  This makes the ground rules very clear.  And above all else, it sends a message to the employee that I plan on trusting them.  It is now clear that sooner or later my goal is to accept their suggestions for solutions to the problems they bring to me.  That is a powerful message of trust.

 “So, make sure you come with at least two viable solutions.”  This is further clarification.  And once again I am reinforcing that I am going to be looking to the employee for the solutions to problems and issues.  I’m also indicating that there is always more than one solution to a problem, that I, as the manger or anybody else for that matter, do not have the corner on viable solutions.  By asking for two viable solutions from the employee I am already indicating that the world is filled with possible solutions and the best solution may not be the most obvious.  I’m also implying that there is no “right” solution.  This message is packed with assumptions and presuppositions that are important for the training of an employee. So whatever you do, never ask for just one solution.  If you do, the employee will try to come up with the “right” one, and since it doesn’t exist you’ll be defeating your purpose of training the employee through trust and delegation.

“Next, I’m going to ask you a lot of questions when you come to me with a problem or issue.”  I’m now giving the employee an understanding of what they can expect when they come to me with a problem or an issue.  I want there to be no surprises.  I’m also setting them up for the next statement I’m going to make.

“I don’t want you to tell me, ‘Well I’ll have to go away and get the answer to that and get back to you.’”  In this statement I’m telling the employee that I already know what most people will do in this situation.  They’ll go away and find the answers to my question.  I’m telling them that this is not acceptable and I’m setting them up for the alternative to this, which is in my next statement.

“If you want to show me that you can think like me, come to me already having thought of all the questions I could ask and have the answers ready.”  This is another key to the success of this process.  I’m telling them that they don’t have to be like me.  They don’t have to talk like me; they don’t have to look like me.  All I want them to do is to have the answers ready to the questions I might ask them.  That will require that they have already asked the questions I’m going to ask or they think I’m going to ask and have the answers ready.  When it becomes clear to me that they ask all the questions that I might ask and they get the answers to those questions in a way that I would understand and accept, then they have completed the process of “thinking” like me and I can begin to trust them to solve problems at least as well and hopefully better than I.  This is the goal and with this statement the employee understands that.

“From my side, I’ll make sure that I ‘think’ out loud so that you begin to understand my thought processes and begin to understand what I expect.”  Finally, I indicate to the employee that I’m not going to make this a guessing game for them and that I’m going to help them in this process.  I’m going to show them the inner-workings of my thought processes.  I’m going to lead them through my thought processes so they can succeed in this process.

An example of this process follows.  Let’s say that I want the employee sitting before me to understand that it is important to me that she take into account other departments and the impact to other departments when she makes a decision, even if it is not obvious that other departments will be affected by the decision.  The first thing I’ll do is state that this is important to me and so our conversation might go something like this:

“I want you to understand that I think it is very important when making any decision to review the potential impact of that decision on all the departments that might even remotely be affected.  In my experience, not doing this has caused considerable disruption to the company and cost a lot of money.  So, I want to avoid this problem by thinking through the impact of our decisions first.  In some cases, this will be a five-minute mental analysis, and in other cases it may take weeks.  So, let’s say you are making this decision.  The first thing you would ask yourself is ‘who else could be affected?’  Now notice that you are not asking yourself who would you like to be notified regarding being affected, or who would you not want to be affected, or who you don’t care if they’re affected?  No.  The question is asked impartially and that is “Who else could be affected?” 

If your answer even remotely is that some other department or people or division or customer might or would be affected, then I want you to not take any action but come back and see me first and together we’ll figure out what to do next.”

As you and your employees continue to live this process you will begin to establish varying levels of trust with different employees.  Some employees will catch on very quickly.  Others will take more time, and still others will never really “get it”.  That’s OK.  Not everyone is suited to work well with you or to think like you.  You don’t have a corner on the best thought processes anyway. They are just your thought processes, nothing more, nothing less.  This is not about getting people to think like you because you can think better than anyone else.  This is getting people to think like you because you have no other way to build and feel trust with them.  It’s in the human code.

So now as you develop varying levels of trust with different employees you can begin to see that delegating is really about giving more or less responsibility to those you trust more or less, and monitoring accordingly.

The following stages outline the possible trust-building process between a manager and an employee:

Stage #1:                  Let’s say you have one employee that you have worked with in the way I’ve described above and they are just starting out.  That is, you don’t have a high level of trust yet.  Under these circumstances you delegate to them those tasks which are not in any way critical but are more tied to the employees’ tasks in general.  You would monitor the employee closely and have frequent discussions about how they view their tasks and the challenges they come up against.  These discussions would be more for an exchange of ideas and status and to see their thinking processes.

Stage #2:                  As this employee continues to succeed and you begin to feel more comfortable with this employees’ thought processes (i.e., you begin to build your level of trust) you begin to give them tasks and responsibilities that are a little more of a “stretch” for them.  You are still monitoring them closely. You have frequent meetings with them but now you are pushing them a little more by giving them responsibilities that include a certain amount of “judgment” on their part.  You are questioning them harder.  The questions you are asking them have much more impact on the organization or project as a whole, and not just on the task itself.  They look at you like you are asking them something that they didn’t know they were supposed to know about and you reassure them that you just want them to think about their role in an expanded way.

Stage #3:                  Next the employee has grown to the point that you feel much more comfortable with their ability to take on responsibility and think like you.  So, you give them a task or project that has a good deal of judgment in it.  You clearly define what the task is, and you clearly define your expectations, but not the process by which you want it done, that is their choice.  (However, before they begin their task, they must explain to you their planned process for performing the task.  This is very important because it gives you an opportunity to see their thought processes and interject your ideas and processes into the discussion as a way to guide them in their thinking.) You still monitor them closely with frequent status meetings but now you seldom give your opinions.  Now you mostly ask questions and if the answer isn’t what you want to hear but it’s not going to kill the project you bite your tongue.  You do not give your opinion but rather guide by asking questions.  Here is where you can make or break the employees’ self-esteem and decision-making ability.  Here is where you become the coach.  Unless the employee is going to crash the project or task, you ask questions and watch.  And if it looks as if the employee is heading toward a crash but they are not there yet and they may be able to turn in the right direction, your goal is to sit back and watch, and monitor them closely so that if they don’t turn to safety, you can intervene and save them.

This is the process of building trust in your employees.  Some employees will advance to Stage 3 and some will remain at Stages 1 or 2.  Whatever occurs in your organization, it should be very clear now that delegation is a gradual, controlled, proactive, and conscious process.

Now suppose you have an employee who has achieved Stage 3 and they make a mistake, what do you do?  The best way to answer this question is to give you a personal example.  I had just such a situation several years ago. 

Donna had become a fantastic employee.  I had trained and coached her exactly as I have described here.  Most of the managers in the company wanted her on their team (after I had trained her).  Her thought processes were as good as mine.  All she lacked was experience.  (Remember it sounds egotistical but I had no other way to evaluate how well Donna was doing. Just getting the job done is only half of what is necessary.)  She got along well with everyone.  She thought far outside of her own area.  I turned over very important tasks to her and she got them accomplished smoothly and efficiently with a maximum of buy-in from everyone involved and a minimum of disruption, which are my preferred criteria for accomplishing my own tasks.

And then one day I got a phone call from a vendor.  Donna had authorized the production of a marketing piece which cost about 20 time more than I had ever expected it to.  Now I couldn’t blame Donna.  I had given her the authority to run this project.  I had trusted her.  We had never discussed what my expectations were regarding the cost of this piece of marketing material.  So, with these pre-conditions in mind, I asked for a meeting with Donna.

The first thing I said was that I was surprised by the cost of the marketing piece.  She indicated that she thought the cost was high, as well, but she felt that we really needed the marketing piece for the marketing event coming up.  She didn’t feel she had any choice because the time frame was such that any vendor who would be willing to do the work would charge the same amount.

I indicated to her that I didn’t think that it was worth it.  I gave her my rationale and my thought processes about alternatives and what I would have done instead.  She indicated that she understood.

Now I had a choice.  I could have stopped the production of the marketing piece.  And yet I had mixed feelings about doing so.  It would be good to have the marketing piece Donna had authorized.  I just thought it was far too expensive.  Finally, I asked Donna if after our discussion she thought it was still worth producing the marketing piece.  She said she did.  I approved her decision and we went to production.

If I had stopped Donnas’ decision, I would have saved a good deal of money.  But by allowing her decision to stand I did several things at once.  First, I got Donna to listen to my rationale about how I would have done it differently.  You can imagine that if I had vetoed her decision, she would have been thinking more about my veto than about the process I suggested she go through the next time she was faced with a similar situation.  Second, through my words and body language, I sent Donna the message that decisions are not always black and white and that reasonable people can have differing views on a subject and that often there isn’t one “right” answer, although there may be a “best” answer based on a variety of parameters.  And third, I sent Donna the message that I trusted her and that I would support her even if her decision differed from mine within certain parameters.  The message was that she didn’t have to be exactly like me and I would still support her.  The price was high.  But the training was priceless.

I cannot emphasize enough to new managers the importance of this type of delegation.  Your job as a manger is not to “delegate”, in the old sense of the term.  Successful delegation is not the “cause” of good management.  Successful delegation is the “result” or “symptom” of good management.  Your job is to use delegation to build your people into self-sufficient employees who can be equal participants in the tasks, projects, goals and outcomes of your organization and company.  Your job as a manager is to build trust between you and your employees, consciously and proactively, so that the degree to which you delegate to each employee is a conscious reflection of your level of trust in them and is a process which has a 98% chance of success.  Your job is not to fail your employees but to teach them all to excel to their maximum potential.  Trust is the foundation upon which you build the house; delegation is the house.

Now suppose you are not the manager, but you are the employee.  It ought to be clear now that the employee can “reverse” much of the process I have described here and modify the discussions by asking questions of the manager.  Questions that will elicit from the manager his or her thinking processes and by understanding the thinking processes of the manager, the employee can align with the manager to build delegation trust at a faster rate.

You can see this is a big topic and I’ll be writing more about it in the future.