AI Guided Management?

Yaniv Preiss
5 min readMay 15, 2023

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With the recent rise of AI capabilities and accessibility, I got curious about whether we can rely on it for managerial practices.

Instead of reading, learning and gaining management skills, getting support from a coach or a mentor, can a first time manager simply ask ChatGPT how to behave? Would they get the desired results and retention if they blindly follow it?

I asked ChatGPT about the topics listed below, in the form of “What is the most effective way to…?” which is how I assume it would have been used in real life.

There is a lot of value in the responses, but nowhere near perfect.
I have found effective advice as well as counter-productive advice.

Obviously, due to the concise nature of the responses, they lack details that contribute to high success rates, and don’t give actionable guidance that is required in practice, like “build trust”.

DALL·E robot pulling the strings of a person like a puppet

1:1s

Effective

Emphasis on building trust and relationship, set regular cadence, come prepared with agenda, avoid distractions, use open-ended questions.
Regarding the content: give feedback, acknowledge achievements, offer guidance, surface areas for improvement, clarify and set goals, discuss career growth, follow up on action items, make it a safe place.

Ineffective

Doesn’t suggest that the 1:1 is for the direct report and they always start with whatever topics they have.

Doesn’t recommend weekly frequency. For example, monthly 1:1 is known to be extremely ineffective.

Promise of confidentiality is plain wrong, because some information necessitates to act in favor of the organization.

Read more on effective 1:1s.

Feedback

Effective

Be specific — behavior and outcome, shortly after an event.

Ineffective

For negative feedback use the “sandwich” approach: start with a positive comment, deliver the constructive criticism, and end with another positive comment. This structure helps soften the impact of negative feedback.
This is known to be ineffective as often the message is vague and the direct report comes out with understanding that things are great.

Encourage your direct report to share their perspective, ask questions, and provide input.
This is known to cause the direct report to justify their behavior and believe they were right even more.

Balance positive and negative feedback.
It is more effective to have a ratio of 5 positives for each negative.

Read more on effective feedback.

Coaching

Effective

Build trust, set clear expectations, provide feedback, adapt to the person.

Ineffective

Mentor, which is something else — general, long term and strategic, usually done not by the direct manager.

Doesn’t really say how to coach, like teaching, showing, pairing, letting the direct report do it, setting check points beforehand and agreeing on a target date.

Building trust is ideally done in 1:1s, not specifically for coaching.

Delegation

Effective

Define objectives, give context, guidelines and expectations, monitor progress and give feedback.

Reasons to delegate: grow others, offload tasks, empower.

Ineffective

The reasons to delegate miss business continuity.

Doesn’t mention the need to acknowledge that the quality will suffer in the beginning, which is a major argument for managers to not delegate.

Doesn’t advise getting the buy-in of the direct report, and deciding on check-ins in advance.

Read more on effective delegation.

OKRs

Effective

Objectives should be ambitious, inspiring, and aligned with the mission and vision, 2–5 measurable key results that define success, align throughout the org, foster collaboration, transparency of progress, track weekly, adapt, learn and improve.

Ineffective

No detailed guidance on key results, like deciding on numeric unambiguous, objective measurements, which is a common mistake.

Highlight of SMART key results where only measurable and time-bound is favorable, and lack of emphasis on outcome over output and initiatives.

No warning to not use for performance management purposes.

Leading and lagging indicators not mentioned.

Read more on effective OKRs.

Time Management

Effective

Set clear goals, prioritize tasks, Eisenhower matrix, break work to smaller chunks, plan, eliminate distractions, block time, avoid multitasking, say no and delegate.

Ineffective

Missing: “If it takes 2 minutes or less, do now, otherwise schedule”, have one system that you trust, reflect actual time spent on calendar, find leverages like automation, documentation and automation.

Read more on effective time management.

Hiring Process

Effective

Define job requirements, create job description, decide who can interview, decide on channels to find candidates, screen resumes, hiring manager interview, culture fit interview, functional interview, behavioral questions, reference checks, hiring decision with interviewers input, offer and onboarding.
Keep speed and candidate experience, improve the process as you go.

Ineffective

Doesn’t guide who does resume screening.

Doesn’t explain what behavioral questions are, which is a key point.

Doesn’t elaborate how to make the most out of the time during the interview.

Doesn’t explain the need to look for reasons to say no.

Doesn’t advise against panel interviews.

Read more on effective hiring.

Individual Development Plan (IDP)

Effective

Identify areas for growth, set clear objectives involving your direct report, break down to small milestones, find resources, give constant feedback in check-ins.

Ineffective

Highlights SMART where measurable and time-bound are more effective.

Misses the importance of objective success criteria.

Doesn’t recommend to constantly find the “next small action” to mitigate unsuccessful deadline driven behavior.

Motivation

Effective

Set clear expectations, provide feedback, create a development plan, delegate, build trust, give autonomy, empower to make decisions, set work-life balance, generate positive atmosphere, understand their needs and doesn’t mention using bonus.

Ineffective

Doesn’t explicitly suggest to find their intrinsic motivation.

Doesn’t mention mastery and purpose.

Doesn’t mention psychological safety and caring for the person.

Doesn’t mention adequate compensation.

Performance Review

Effective

Gather all information beforehand, such as metrics, outcomes against the career ladder and expectations set, examples, and compare to the direct report’s self assessment, collaborate on development goals.

Ineffective

Claims that the goal is to give feedback and provide growth. It’s incorrect — the purpose is succession planning and having data for compensation and promotion discussions. Feedback and growth are to be given constantly.

Doesn’t insist on a single clear message.

Doesn’t recommend to constantly document information about the direct report’s behavior and outcome.

What does that ChatGPT say when asked “To what extent should I rely on you regarding management practices?”

Effective management guidelines are timeless rather than timely, but it gives disclaimers about insights limited to 2021 and missing latest trends.

Bottom line, it recommends not to rely on it, and to conduct additional research, use expert advice and practical experience.

As an AI language model, I can provide information and insights on various management practices based on the knowledge available to me up until September 2021. However, it’s important to note that I do not have real-time access to the latest developments and trends in the field of management.

While I can offer guidance and suggestions, it’s crucial to exercise critical thinking and consider multiple sources of information when making management decisions. It’s always advisable to consult with experts, conduct independent research, and take into account the specific context and circumstances of your organization or situation.

Remember that management practices can vary depending on industry, company size, culture, and other factors. What works for one organization may not necessarily be suitable for another. Therefore, it’s essential to adapt and tailor management approaches to suit your specific needs and goals.

In summary, while I can provide valuable insights and information on management practices, it is important to supplement it with additional research, expert advice, and practical experience to make well-informed decisions.

Effective leadership is learned
To learn more or reach out, visit my website or LinkedIn

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Yaniv Preiss
Yaniv Preiss

Written by Yaniv Preiss

Coaching managers to become effective | Head Of Engineering | I write about management, leadership and tech

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