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  • Writer's pictureJohn Graham

How to Build a Learning Organization: Step 3 - Coaching

In our prior posts, we talked about the importance of training and mentoring. These activities are part of how to share what your organization has learned with new hires and acquired hires. They are a crucial part of how to scale your organization.

We've been using the Dreyfus model of skill acquisition and Situational Leadership to guide our solutions to building a learning organization.

This post will deal with the top left quadrant of the Situational Leadership matrix - behaviors that the model calls "Participating" or "Supporting," but we will call "Coaching."

(Situational leadership uses the term "Coaching" for the top right of its matrix. We called that "mentoring.")

Additionally, we'll be answering the question of how to Competent people into Proficient people.

By the end of this post, I hope to have answered the following questions:

  • What is Coaching as defined by Guildmaster, and who should do it?

  • How does Coaching solve the "Supporting" problem in situational leadership?

  • How does Coaching solve the "Competent" to "Proficient" pain in the Dreyfus model?

  • In what activities would a successful Coach partake?

A reminder: Coaching can improve productivity by 4x when combined with other methods. This improvement would come across both the "Coaching" and "Mentoring" styles described in this post and the previous one.

Heard enough already and want some management coaching yourself? Or does this all sound good, but you want someone to help you with the execution? Contact us!

What is Coaching?

Coaching, to Guildmaster, is when a person tries to help another person who may know as much or more than they do.

The best metaphor is, well, a coach.

A pitching coach on a baseball team is not the best pitcher. That'd be kind of absurd. Now, they may have been a reasonable pitcher at one time, and experience certainly makes a coach better.

We use this definition to differentiate Coaching from Mentoring, which we defined in the Mentoring post as a person who knows more than their mentee helping their mentee.

Who Does the Coaching?

Coaching is a valuable skill for anyone and everyone to learn because it is universally applicable. No matter who has the problem at hand, someone can help coach that person through it.

Let's put this definition of coaching inside our Learning Organization so far.

Who's doing the training? You probably have developed some written curricula or brought in outside trainers to do the training. Perhaps your more senior technical staff also do live trainings.

Who's doing the mentoring? As stated in the mentoring blog, you will use the Dreyfus Squared approach. So, your Competent folks will mentor your Advanced Beginners, and so on.

That leaves the question, who does the Coaching then? Who specializes in Coaching? This would be your people managers, and Coaching becomes one of the main parts of their job.

At Guildmaster, we strongly recommend a "federalism" approach to management. That means many different management chains whose roles, responsibilities, and relationships are clearly defined. We don't actually have a "just-a-manager" role that we'd recommend. That would consolidate power too much.

Most management functions are subsumed into project, product, or technical management (these are your staff engineers and above). What's left for a traditional "manager" to do? These remaining tasks are what we call "People Management."

And one of the main day-to-day activities of these "People Managers" is coaching.

We're not advocating you "coach" only your Competent folks, even though it's emerging here in step 3. All people managers should coach their direct reports, and all direct reports have a people manager.

How Does This Solve Our Problem?

Coaching comes into play on step three because the air is becoming a bit rarefied. You're not going to have as many Proficient people to mentor your Competent people (or you're bootstrapping and have zero Proficient people).

You will have fewer training and mentoring resources overall for this step. Coaching is becoming the primary means of growing people since your other means of growing people are tapering due to the difficulty of the problem (hard to train at this level) and the lack of resources (you have fewer mentors at this level).

In other words, if you're getting people stuck at Competent, the solution is to grow better Coaches and Coaching as a discipline.

Each step also tends to slow down in its ability to graduate folks to the next level due to the same problem. Novices and Advanced Beginners have lots of excellent training (which is very, very effective), a plethora of good mentors (who are very effective), and a people manager (who is effective) at growing them.

Because we have fewer resources at each step, and because our resources are less effective, people should expect to spend more time here.

Getting out of Novice may take folks only 6 months or so. Moving from Advanced Beginner to Competent may take two or so years. But moving from Competent to Proficient can take a bit longer.

What about Training?

I implied that training at this level has become more rarefied; but it hasn't been extinguished.

At this level, training is going to look more like sampling. Competent and above folks may try out various trainings at Conferences, and they may not be "regular" enough to recommend a curriculum. They may also be looking at a lot of Conference talks.

Depending on the maturity of the discipline, there may be "advanced" books that get introduced at this level. Like conferences, things are a little less rigorous in terms of schedule.

What training best looks like at this level is some sort of self-guided "continuing education." So yes, training courses, but no set curriculum, guided by the individual on their interest and generally leaning towards more cutting edge or advanced techniques.

A fantastic internal training pattern would be tech talks. Folks can put together a presentation on something they know (or use the creation of a presentation as an excuse to learn something they want to know) and then share it with the rest of the staff. Regular tech talks - as well as their recordings and exercises - become an excellent continuing education source.

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What about Mentoring?

If you're using the Dreyfus Squared model, you will want to pair up Competent people with Proficient people to grow them. But you may be running out of Proficient people.

Ensuring Competent people are actively mentoring Advanced Beginners is another tactic to keep Competent people growing. The best way to learn is to teach.

Mentoring can and should continue. It may be more challenging since there will be fewer and fewer resources readily available for mentors to utilize, it will become more labor-intensive. This is precisely at the same time that fewer Proficient people are available, so doubling or tripling up mentors might be turning mentoring into a full-time job.

Q: Is this what Guildmaster offers when it offers "Management Coaching?"
A: If you're interested in management coaching services for either yourself or your team, you'd get our help with all three initial steps of the learning organization: management training, management mentoring, and this style of Coaching.
Additionally, we'd be able to advise on the next two steps tailored for your needs: how to delegate authority and design your organization and how to create thought leaders. Interested? Contact us!

What about Feedback?

We put feedback as a tool precious for influential mentors. But, it's also an invaluable tool for Coaching and Coaches.

The difference is the target of the feedback.

Since Coaches are by definition "the same as, or not as good as" the coached in terms of the domain they're being coached on, feedback will be less and less on technical disciplines and more and more on behavioral domains.

As we'll discuss later, your People Managers are the front-line defenders of your company's values; and their feedback will relate primarily to following those values.

This is important because the more technically skilled individuals get, the more power they have. A company's culture is little more than the sum of all individuals' values times their power. Because of the increased power for Proficient people, they must ensure they are being examples of the company's values.

Culture can be roughly thought of as a weighted average of everyone's values in the organization, with the weights being set to the the amount of power that person has in the organization, or...
... where K is the number of people in the organization

How does Coaching Help

Coaching helps people continue to grow in three ways:

  1. It keeps people's spirits up despite setbacks...

  2. while ensuring there are, indeed, SOME setbacks (things should not be too easy)...

  3. while providing an objective third party viewpoint of someone's growth

How Coaches keep Spirits Up

The most effective tool coaching has for increasing morale is active listening.

Many people don't want their problems solved; they often value autonomy in being empowered to solve problems themselves. Additionally, the problems coaches generally encounter aren't problems they can solve. They either lack the power or the expertise.

What a coach can do is help an individual feel heard.

How Coaches Keep People Challenged

If one half of Coaching is active listening, the other half is asking good questions. Again, Coaches cannot and should not have the answers. But they can ensure they're asking the right questions.

The more experiences a Competent person has that are at the edge of their skills set, the closer they'll get to Proficient if they take away the "right" lessons from each experience.

A coach doesn't prescribe the correct lesson is; they help identify patterns of unhelpful answers. Asking the right questions helps reframe challenges into something solvable - given suitable approaches (experiments, research, or something else).

In this way, the Coach is acting as a third party. They understand the presenting issues through active listening. They've used good questions to further explore and reframe things in a way the coached can be overcome. Finally, they know their audience very well. They see the thought patterns the coached individual suffered in the past and may be experiencing in the present.

It feels very different to be outside someone's skull than inside. An external perspective is practically the only help a person can offer when no one can provide the correct answer.

In other words, the individual being coached is the solution finding machine. The Coach cannot find solutions. However, the Coach specializes in knowing how to debug and maintain solution-finding machines.

How Can Coaching Help Competent People Become Proficient?

What this all creates is a curated, guided experience. In other words, sheer experience - as in, years of experience - can teach us some things if we try. We're still applying the principles of progressive overload and always trying to learn and apply something new.

But raw uncoached experience has obviously led plenty of people to just spin their wheels for years. A Coach ensures that doesn't happen. They can't fast-forward progress; but a Coach can often spot when someone isn't growing and diagnose why.

People stop growing not because the problem is too complex. After all, the problem's difficulty can change the rate at which they grow but not push it to zero. Instead, they stop growing more than likely because of some thought pattern in themselves.

When facing a new problem, a coach is there to hear about the situation, keep track of your progress, ask questions that help you uncover the real problem, and remind you of your own strengths and weaknesses as they surface. These curated, guided experiences are the coaching version of deliberate practice.

Since feedback from experience isn't a given (unlike deliberate practice), the Coach helps ensure successes and failures are analyzed in as unbiased a way as possible to continue improving.

What Makes a Successful Coach?

We just talked about a few tools a successful coach needs:

  • The ability to active listen

  • The ability to ask insightful questions

But there are other traits about a Coach and a Coaching Program that help it find success. Namely:

  • Coaches should have a high EQ

  • Coaches should have knowledge of sticking points

  • Coaching Programs should have rotations

  • Coaches should exemplify values

These traits highlight the significance of Emotional Intelligence (or EQ). Indeed, EQ is one of the more predictive traits (other than management knowledge) of good managers.

EQ can be grown, though that's beyond the scope of this blog post.

Knowledge of the Usual Sticking Points

The actual domain knowledge a Coach might want - beyond the skills of active listening and insightful questions - is the very domain that helps create the insightful questions. It is knowledge of common human failure points.

We will break these negative thought patterns into three categories, then introduce a fourth category that could be considered a "positive thought pattern."

In many cases, identifying these patterns and challenging them takes a bit of a "Devil's Advocate." As a Coach, you'll need to interrogate the framing of the problem as it's presented. This means asking probing and sometimes tricky questions - but still good questions.

Logical Fallacies

This category of thinking basically sounds right but actually isn't. Logical fallacies are errors in how people arrive at conclusions from their assumptions.

What we're most interested in are the "informal" fallacies. You can find a great list here.

Coaching through logical fallacies is NOT about "gotchya" moments. Instead, you want to identify the error. Work with the coached about how their assumptions don't necessarily lead to their conclusions. Then, and only then, might you work together to determine what conclusions their beliefs actually lead to - if any!

Cognitive Biases

These flaws are related to how our minds process information - the heuristics they use that lead to faulty conclusions.

While logical fallacies are often socialized - learned and used so much despite being false - cognitive biases often come built-in. So that's... swell?

As always, it's not about having a "gotchya" moment but rather walking the person through why their beliefs about the world may not actually reflect the world.

If you've noticed, many of these flaws in reasoning happen without the person knowing. Being an objective third party helps you spot them far more quickly than the person in the weeds of the problem. Moreover, spotting them and working through them doesn't require any domain knowledge of the problem being solved, but rather domain knowledge of the flawed reasoning itself.

Negative Thought Patterns

Negative thought patterns are like cognitive biases; they come built into the way our minds work. While cognitive biases are heuristics our mind uses to arrive at conclusions, negative thought patterns result from flaws in where our minds decide to spend their resources and attention.

Not everyone suffers from these equally. You'll probably find folks who score a little higher on Emotionality/Neuroticism to struggle with these more often.

As Coaches, we're not therapists; and we're not qualified to diagnose or treat anything beyond what might be keeping someone from solving a technical problem at work. But no one's stopping a Coach from asking the question, "Hey, are you catastrophizing here? What's the worst that can happen?"

From an HR perspective, ensuring your employees have access to mental health resources and are encouraged to use them can actually be a cost savings/productivity boost for people managers. Two the author has liked are:

These can help people remain engaged, help build emotional intelligence, and build better managers.

Positive Thought Patterns: Mental Models

Mental models and guiding metaphors are the flip sides of identifying logical flaws. They're basically nice little heuristics that work more often than not. The only problem is, you have to have been exposed to them.

Having a broad knowledge of various mental models and brainstorming where they might apply can help people break through in challenging areas. Mental models apply to a wide range of fields in non-intuitive ways. Though they're just metaphors, they're metaphors that can help people fill in the gaps.

So you may have someone on your team who's mentally stuck. You think one or two mental models may apply through your active listening and good questions.

Applying Occam's razor or the physical idea of Friction and Velocity may seem off the wall; but these ideas tend to have something to teach us about a LOT of new domains. Or, they can bootstrap us into understanding those domains better.

A good list of mental models is here, but there is no exhaustive list. Just try to find ways to apply your hobbies and other disciplines to the problem at hand!

Experience Patterns: The Rotation

If Coaching is about guided experiences, then one big part of those guided experiences is to make sure you hear from multiple coaches and have different experiences.

This means a big part of the transition from Competent to Proficient would be rotations and variety in general.

For example, to become Proficient in C++, you need to work on all aspects of C++. This might require you to move to different teams that are currently trying to solve other parts of the business problem by leveraging various aspects of C++.

Or alternatively, to truly be Proficient in C++, you might need to be an Advanced Beginner in Haskell.

Starting Strength is about strength training and a good mental model (Tada!) for how to grow just about anything. It argues that "variety" is an advanced training method only to be done when the basics of hitting core exercises have hit some limit.

You're starting to get there if you're trying to become Proficient. You need to go deeper AND wider; this will take time. If you seek out these experiences AND have a coach to help guide you through them, it's nearly impossible not to become Proficient and beyond.

Honesty and Humility

The last trait that's important for being a good Coach and People manager is exemplifying the values of Honesty and Humility.

First, you need to know your own limits. You're not there to solve peoples' problems because you can't. And you also need to understand that you're never going to understand the issues (no matter how well you listen and ask questions) as well as the person you're coaching.

You've always got to be willing to step back and re-evaluate.

Second, you've got to be honest with the recipients of your Coaching. Coaching is a tricky balance of soft and tough love. You want people to stay motivated despite setbacks. But you also need to ensure they're being challenged. They may squeal a little when they're being challenged. It's not always comfortable.

It helps to be honest about what someone needs. You've got to be willing to play the Devil's Advocate when the time warrants it to help sharpen the person you're trying to coach.

While all employees need to model a company's values to a certain extent; people managers must model and share these values.

If, for example, you try and hire people in the top 66th percentile in honesty and humility, you may only want to consider people in the top 50th percentile or 33rd percentile for people manager positions.

People managers exemplify the company's strategy when it comes to that company's values. You want them to share those values more than the average employee.

Great Resources

We've covered several great resources, but I'd also highly recommend these for any "People Manager" training:


We're nearing the end of most of what is needed for a learning organization. By the time people are Competent growing into Proficient, they can take on a wide variety of roles in the organization requiring those skills.

Training will continue - largely more ad-hoc, external (conferences), and self-guided - at this stage. Mentoring will also continue as it can. And while Coaching is introduced here because of its importance in growing Proficiency from Competence, all employees need a coach in their direct People Manager.

The keys to coaching well are active listening and asking good questions. This requires emotional intelligence, honesty, and humility to do well. Finally, one can ask better questions the more one knows about the common traps people get stuck in and typical patterns that occur no matter the discipline.

Coaching is just one aspect of growing Competence into Proficiency - rotations and varied experiences are the other ingredients.

We'll discuss Delegation next - the final step in situational leadership and the second to last in the Dreyfus model. Finally, we'll talk about how to actually grow expertise in the company's core competencies.

If you want help developing your own ideas for a Learning Organization, or, alternatively, need Management Coaching to grow yourself from Competent, please reach out to us or...

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