W.I.L.L. – What does Ideal Look Like? The 10-minute Coaching 1-on-1

What does Ideal Look Like? (W.I.L.L.)

The Key Pillars of Coaching Moments

In every 1-on-1, there are 4 key pillars to your new ‘Coaching Moments’:
1. Preparation
2. Decision-Making Framework
3. Eureka Moment
4. Action

Let’s take a journey through an example of a best-in-class 1-on-1:

Step 1: Preparation

Preparation is often overlooked or ignored, but will become the largest time commitment to your process. Before the meeting, ensure this is complete.

– Send the suggested topic for the meeting to the seller (based on the 4-week schedule in our Basic Principles video).
– Ask the seller if they have a request or needed coaching moment.
– Request the seller to detail their decisions and actions for you to review in advance of the meeting.

Remember, accountability is a 2-way street. You are accountable to communicating what you need to prepare, and the seller clearly understands what they need to provide to you and when.

Your goal is to digest the materials in advance (think Operational Tasks), and develop your Decision-Making Framework independent of the seller. This helps you formulate your appropriate WHAT and HOW questions, and prepare your Gestalt coaching moment should/if you see ‘Red Flags’ in their structured thinking.

Ultimately, you are what you tolerate. Top leaders will not allow the 1-on-1 meeting to run if the seller is not prepared in advance. If someone isn’t prepared, sometimes the best course of action is to end the meeting.

The seller must be prepared to present their thinking and defend their Decision-Making Framework during the meeting.

Step 2: Leverage the Decision-Making Framework

After you’ve prepared and done your due diligence, it’s now time to use your Decision-Making Framework. Why? Because it’s the best way to level up the skills of sellers’ and create future leaders.

Begin the meeting by outlining the agenda. Here are 3 battle-tested concepts to include in the agenda that will increase gestalt, decision making, and eureka moments!

1. What is the inflection point that we’ll begin to analyze?
2. What was your Decision-Making criteria?
3. After we review together, how would you evaluate your decision-making process? And what (if anything) would you have done differently.

Role Play Example: Prioritizing the Nike account

You: I reviewed your details on the Nike account. Thank you for sending everything in advance. What I would like to better understand is your decision to focus most of your energy this month on growing their workloads. Why don’t you draw out your decision-making tree for me so we can collaborate on it.

SELLER: I noticed two compelling triggers and signals: A. Their IT team was consuming some of our new insights last week. B. I then noticed that they hired a new CISO from Adidas last month.

You: What specifically about these compelling triggers and signals makes you believe you can grow the account?

SELLER: I think they might be interested in Cloud Migration for their new wearables division on market insights, and their new CISO came from Adidas that shifted to the cloud 18 months ago according to our data.

You: What insights about that CISO have you uncovered that will help you shape your conversation? And how is his experience with AWS going to adversely slow down/kill a deal?

SELLER: Experience with AWS? Really?

You: Let’s pause right here.

Time to Implement Gestalt & Coach Through Stories

It’s now time to execute gestalt. Leaders educate through stories that are situational and provide empirical evidence of reframing a sellers’ decision-making process.

Role Play Example:

SELLER: Experience with our competitor? Really?

You: 3 years ago, I had decided to target Vodafone using the exact same logic. There was a new CIO, the telecom industry was shifting from 4G to 5G, and it appeared the stars were aligning in my favor. I initially reached out to the CIO who pushed me down to the Director of IT Infrastructure who really liked our ideas. That director formed a committee to review, we had cross-functional meetings, and they scoped expanding workloads. The new CIO got word of our project, but what we didn’t know is that he spoke at an AWS conference the year before, and had experience with their solution when he worked at Tesco. He called his old colleagues at AWS and sidestepped our workload project. The problem is that this deal took 18 months to materialize, a huge amount of internal resources, and created a large churn gap in my portfolio.

Step 3: Help Spark the Eureka Moment

This is your value creation moment. Allow the seller to retrace their decisions using structured thinking, allowing the decision-making tree to be a visual aid. This “Teach Back Method” is a powerful model to accelerate their Eureka Moment. If your Sellers can teach back an improved decision-making plan, they are now empowered to retain those skills for the future.

Example questions:


– How will you gather competitive intelligence on Nike or any of your key accounts in the future?
– What is your action plan with Nike to avoid similar mistakes?
– Knowing what you know now, HOW would you execute your Decision-Making Framework again?

Step 4: Time to Take Action

Finally, this is where both you and the seller assess the following:

a. Are your actions a “Green Flag”? If so, stay the course;
b. Or a “Red Flag”? If so, adjust your course of action.

If there is a “Red Flag”, introduce Resource Allocation (your 3rd core role & responsibility). Discuss the people, process and/or technology internally or externally that can help adjust the course.

Then document an accountability plan for next steps:
a. What are both parties’ next steps?
b. When are they due?
c. What are the clear expectations and the expected results by that due date?

Executing this feedback loop 52 times a year will highly influence strong sales habits and drive towards your sales objectives.

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