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Team Performance

How to Delegate Effectively: Crash the Car, Don't Drive Off a Cliff

By Camden McGregor 6 min read

If a leader is scared of failure, it clouds their judgment, and that fear spreads to the team. When your team is afraid to fail, they stop taking risks and run back to the leader with every question.

The business is stuck, and the leader is the reason. Learning how to delegate effectively is really about giving your team a safe zone to fail in, because without one you stay the leadership bottleneck until you eventually burn out.

I covered why that matters in the first part of this series on how to stop micromanaging. This one is the build. Follow this framework and you can craft guardrails for each member of your team that give them room to experiment and grow.

Think about hiring a new copywriter. The first few weeks you review all materials before they go out. After that you check materials a few times a week. Eventually you stop checking and let that copywriter do their job to the fullest. Prevent catastrophic failure while allowing room for smaller, safer failures.

Two ways to build guardrails

There are two options when it comes to creating guardrails in your business: intervention or built-in guardrails.

An intervention is necessary when the potential failure is catastrophic or the training process is very time-consuming. In an intervention, you scaffold around the position to keep operations moving if you can, then you remove the team member in question and give them the training they need to succeed.

Built-in guardrails work the other way. They create a safe zone for controlled failure during operations, so the team keeps moving forward without risking catastrophic failures.

Most roles need both at different points in their life.

Interventions: train before the whirlwind takes over

New-hire training is a great example of an intervention. You intervene before someone can learn bad habits or cause damage to the business.

Too many leadership teams focus on fast training and getting new hires productive quickly. There is real value in speed, but fixing problems on the fly is much harder than fixing them in a training environment.

That whirlwind of daily to-dos can paralyze just about anyone. The investment in an intervention has a much better ROI early on.

For existing hires who need an intervention, a retreat or offsite is usually the only thing that works, because you have to break the whirlwind before anyone can make meaningful changes. It is hard to set aside the time for something like a company offsite. The alternative is a team doomed to stay exactly where it is now, stagnant and overwhelmed.

Built-in guardrails: the copywriter example

When designed properly, built-in guardrails do three jobs at once. They keep the team safe, they allow freedom to experiment, and they move you away from micromanagement.

Go back to the copywriter. In a larger company it is necessary to review all materials before they go public. When any typo or piece of misinformation can cost your company millions of dollars, that copywriter's guardrails have to be tight to start.

Even at that stage there is still freedom. The alternative would be writing each piece of copy together for the first few weeks, which I am sure would scare off most copywriters. Instead you give them space to experiment while protecting the business from the failures you cannot absorb.

A copywriter at a smaller company with less risk may start with much wider guardrails. "Don't talk about X, Y, or Z, and focus on selling A, B, and C. Besides that, do what you think is best."

You still check the copy occasionally for quality control. But that new team member gets to grow in the role, because the job description is now "do what you think is best." Allowing for personal taste gives them a chance to buy in and make the job their own.

How to delegate tasks on a sales team without a script

Say you are building out a sales team. The micromanagement model, the bottleneck model, is to have them follow the script word-for-word and check with the boss anytime something goes off script.

How exciting does that job sound? The people who are best at sales know when to leave the script. Running that model limits your team's potential and makes their work boring and predictable.

The guardrail model looks like this instead:

  1. Use the script for the first ten calls with little to no improvisation.
  2. After that, they can leave the script, but they must never talk about X, Y, or Z and they cannot offer any discounts or deals.
  3. A few weeks later, give them the freedom to adjust the offer or add discounts.

Same role, same risk profile, completely different ceiling.

The four keys to designing guardrails

There are four keys to designing guardrails:

  1. The failures have to be real enough to learn from. If people are too protected from consequences, they never learn the reality of risk. If you got a do-over for everything, would you try hard the first time? Consequences drive performance, and we cannot eliminate them entirely.
  2. The guardrails have to protect from catastrophic failures. It would be irresponsible for a leader not to protect their team from consequences that cannot be undone. Sometimes an employee needs to crash their car. It is the leader's job to build the guardrails so they do not just drive straight off a cliff.
  3. You have to outline clear boundaries. Vague rules are impossible to follow.
  4. You have to progressively loosen the guardrails as the team member improves. Let them grow. Great leaders work themselves out of their job.

Clear boundaries plus unanswered questions build curiosity

Clear boundaries do more than keep people safe. They also train people to look for other options.

When I am coaching rugby and introducing a new drill or game, I define some clear boundaries and deliberately leave some things unexplained. Why? Because it trains the players to ask questions and go looking for more information.

That is the power of combining clear boundaries with room to experiment. You create a culture of curiosity that drives growth and innovation.

Self leadership is what makes guardrails hold

Interventions and built-in guardrails are effective tools, but one leadership skill decides how well they work: self leadership.

Great leaders do not just lead followers. They teach their team how to lead, so they end up leading a team of leaders: people who understand the vision, want to grow, own their problem sets, and can hold themselves accountable when things go wrong.

You have to lead yourself if you want to lead others, so building a team of leaders starts with teaching them to lead themselves. Planning, setting goals, communicating a vision, and installing guardrails all work in your own life, not just in the business.

Great leaders model that by leading in every area of their life and showing their commitment to learning and growth. Modeling is the best way to inspire change in others. That, and paying for proper training.

How to teach your team to manage their own guardrails

So how do you teach your team to lead themselves?

  1. Start with the why. Teach them the reasoning behind everything they do.
  2. Give them freedom to diagnose problems themselves. They work most closely with their projects, so they have the best skillset for diagnosing what they run into.
  3. Give them permission to solve the problem themselves. They should not have to run every solution by you. Let them make the best choice they see.

What underpins all three is modeling the behavior yourself. What are your guardrails?

Pick one guardrail and install it

These guardrail frameworks will help your team function more independently, get better at their jobs, and enjoy their work more. Buy-in is powerful, and one of the best sources of buy-in is ownership of the plan and the problem-solving process.

If you fail to install guardrails, you stay the bottleneck. You will micromanage things and have some success, but it will be nothing compared to what you would get by giving your team the freedom to experiment.

Inside the Steel Men Tribe we have helped several members build these guardrails for themselves and their teams to unlock the next level of performance. If you need help installing guardrails for your team, learn more about Steel Men. For more stories on why this matters, watch my video on installing guardrails.

What is one guardrail you need to add to your own life? What impact would it have? How could you do the same thing for your team? Practice this skill leading yourself and you will find better ways to use it leading your team.

Find the gap before it costs you

Score your team against the 7 C's of Leadership in about ten minutes, then talk it through with Otis.

Take the 7 C's assessment

Frequently asked questions

How do I delegate effectively without losing control?

Install guardrails instead of approvals. Define clear boundaries for the role, make sure a mistake inside those boundaries is survivable, check the work on a schedule rather than every time, and widen the boundaries as the person proves out.

What is the difference between an intervention and a built-in guardrail?

An intervention pulls someone out of operations for dedicated training, which you do when the potential failure is catastrophic or the training is time-consuming. A built-in guardrail stays in place during operations and creates a safe zone for controlled failure while the work continues.

How do I stop being the bottleneck in my business?

Stop requiring that every decision come back to you. Teach the why behind the work, let your team diagnose their own problems, and give them permission to act on the solution they see rather than clearing it with you first.

What is self leadership and why does it matter for delegation?

Self leadership is leading yourself before you lead others: planning, setting goals, holding yourself accountable, and installing your own guardrails. It matters because a team of leaders only forms when the people on it can manage their own boundaries, and modeling that behavior is how you teach it.

How tight should guardrails be for a new hire?

As tight as the risk requires and no tighter. A copywriter at a company where one typo costs millions gets everything reviewed before it goes public. A copywriter at a smaller company can start with "avoid these topics, sell these things, otherwise do what you think is best."

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