Is It Time for a Copilot Prompting Health Check?

As Copilot has been with us in some guise or other since Februrary 2023 you’ve been flexing your prompting muscles for a while now so there’s a good chance you’ve improved dramatically without even realising it. Many of us started with prompts like: Summarise this document.  And now, you are probably writing prompts that go well beyond GCSE (Goal, Context, Source, Expectations).

But here’s a question: When was the last time you checked in on your prompting skills?

Copilot is evolving rapidly. New features arrive regularly. Context windows are improving. Agent experiences continue to develop. What worked brilliantly six months ago might not be the most effective approach today.  And you have an prompting expert, literally at your finger tips.  So why not ask your Copilot to help you review your prompting techniques and how you could evolve further to take advantage of newer techniques and increases in functionality.

A Prompt Worth Trying

Try asking Copilot to analyse your own usage patterns:

Looking back at my prompts and chats, can you tell me:
• What is my favourite prompting technique?
• What type of tasks do I use Copilot for most often?
• What prompting approaches do I use less frequently?
• Which techniques could have the greatest impact if I started using them more often?
• What am I already doing particularly well?
• Give me practical suggestions for improving my prompting skills over the next three months.

The results can be surprisingly revealing.

You may discover that you are a premium prompter and have nothing to learn, but its more likely you’ll discover new techniques that unlock even more value.

What I Learned From My Own Prompt Review

When I ran this exercise, Copilot identified several recurring patterns.

My Favourite Prompting Technique

Apparently, my strongest technique is iterative refinement.

Rather than expecting the perfect answer from a single prompt, I tend to:

1. Generate a first draft
2. Review the output
3. Narrow the scope
4. Adjust specific elements
5. Refine repeatedly until the result meets my needs

Examples include:

• Course development and workbook creation
• Self-build planning and design decisions
• Logo and branding work
• Event planning and logistics
• Content creation and blog writing

Apparently, I use Copilot more like a collaborative colleague than a search engine.  But the interesting observation wasn’t what I use Copilot for.  It was what I don’t use it for often enough.

High-Impact Prompting Techniques I Should Use More Often

1. Deliberate Contradiction Prompting

Most people ask Copilot to support an idea, but try asking it to challenge your thinking, getting not agreement but help making better decisions but considering alternative views.

Try:

Challenge my preferred approach.Identify weaknesses, risks, assumptions and blind spots.
Provide three alternative approaches and explain why they might be better.

2. Decision Matrix Prompting

I frequently compare options.  What I rarely do is ask Copilot to score them systematically. This often exposes assumptions hidden inside our preferences.

Try:

Create a weighted decision matrix comparing these options.
Score each against:
• Cost
• Risk
• Complexity
• Implementation effort
• Long-term value
• Ongoing maintenance
Show the calculations and explain the outcome.

3. Red Team Reviews

One of the most powerful techniques available is to ask Copilot to become your toughest critic. Sometimes the most valuable Copilot response is the one you hope not to receive.

Act as an independent reviewer.Assume this proposal has significant weaknesses.
Identify:
• Risks
• Gaps
• Unrealistic assumptions
• Missing information
• Potential causes of failure
Do not be polite. Be objective.

4. Scenario Simulation

Instead of analysing information, ask Copilot to simulate situations. Simulation encourages us to think ahead rather than merely reacting.

Example: Training Delivery

Simulate five challenging delegates attending a Copilot training course.
Give each a different personality, role and concern.
Generate the questions they are most likely to ask and suggest effective responses.

Example: Planning Applications

Act as a planning officer reviewing this proposal.
Identify concerns, questions and information that would improve my chances of approval.

Example: Compliance Reviews

Act as a VAT inspector reviewing this evidence.
What questions would you ask and what concerns might you raise?

5. Multi-Expert Panels

A single answer often reflects a single perspective.  Why not ask for several?  This is something my son has also suggested based on his use of Copilot in helping him review and draft academic papers.  Copilot suggested I would find it particualry helpful for Microsoft 365 governance, Copilot adoption and organisational change projects especially in revealling stakeholder concerns before they become real problems.

Review this proposal from the perspective of:
• A trainer
• A business owner
• A CFO
• An IT administrator
• A compliance officer
• An end user
Highlight where their views agree and where they differ.

The Real Opportunity

My biggest takeaway fromt his exercise wasn’t that I need better prompt wording. It was that I could use Copilot slightly differently for the same tasks and get even more value.

Most of us are already using Copilot as a researcher, a writer, a summariser and an information finder

The next stage for me apprently is to use it as a red team reviewer, a decision architect, a risk analyst, a task/project planning adviser and a scenario simulator

So here’s my challenge to you:

Ask Copilot to review your prompting habits.

You might discover that your greatest opportunity isn’t learning a new prompt.  It’s learning a new way to think about the prompts you’re already writing.

After all, every day is a learning day. 😉