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7 essential decision-making frameworks (plus 3 new Chief of Staff jobs)

The Pugh Matrix, Conviction Scale, "Safe to Try" test, SPADE, and more, plus referral rewards, a candidate close-up, and more


But First, 3 Shower Thoughts:

  1. The bar for quality content has never been higher.

  2. A simple way to build trust: actually do what you’ll say you’ll do.

  3. Focus on what you want to see more of.


There's a Framework For That

I’m a glutton for a great decision-making framework. While they’re not perfect, they are sufficient and come in handy in countless situations. Here are a few of my favorites:

The Eisenhower Matrix

President Dwight D. Eisenhower once said:

I have two kinds of problems, the urgent and the important. The urgent are not important, and the important are never urgent.

Stephen Covey, author of The 7 Habits of Highly Effective People, actually created the matrix we use today, the purpose of which is to prioritize tasks based on their urgency and importance.

Essentially, you need to:

  • DO tasks that are important & urgent

  • SCHEDULE tasks that are important but not urgent

  • DELEGATE tasks that are not important but are urgent

  • DELETE tasks that are neither important nor urgent

The Eisenhower Matrix…but make it Right Hand branded.

This matrix helps you avoid the “Mere-Urgency Effect”, which is our tendency to focus on completing more urgent tasks even though the less urgent ones offer a greater reward.

The Conviction Scale

This is a quick and dirty way to gauge the directionality and strength of confidence in a decision or idea.

I’ve seen it used effectively by hiring panels to surface areas of disagreement and drive discussion among interviewers. The meaning of the numbers is described below.

-2 = I wouldn’t recommend hiring this person, and I’d be upset if we did

-1 = I wouldn’t recommend hiring this person, but I can be convinced otherwise

+1 = I would recommend hiring this person, but I can be convinced otherwise

+2 = I would recommend hiring this person, and I’d be upset if we didn’t

In this example, the conviction scale does a couple of things. It:

  • Captures a panel’s thoughts more accurately than a simple yes/no vote

  • Gives space for positive and negative feedback, bringing out potential areas of contention or consensus in the group

  • Doesn’t make space for a middle ground (there is no vote for “0”, and this is by design) — you either want this person as your colleague, or you don’t

  • Encourages discussion, above all

No framework is perfect, but using this more rudimentary approach might make sense in the earlier days of a startup when robust processes and systems around hiring are simply lacking and where decisions are more consensus-based.

You can also adapt the conviction scale to your situation with custom definitions, but the back half of the statement that captures sentiment should remain the same.

The Pugh Matrix

This framework comes in handy when you need to compare various solutions or options against a set of weighted criteria.

Instructions for Use:

  • Assign a weight to each criterion based on its importance.

  • For each option A, B, or C:

  • Assign a ‘+’ if it is better than the baseline option

  • Assign a ‘-’ if it is worse than the baseline option

  • Assign a ‘0’ if it is the same as the baseline option

  • Multiply the weight by +1 for a ‘+’, -1 for a ‘-’, and 0 for a ‘0’.

  • The "Weighted Total Score" is the sum of the "Weighted Sum of Positives" and "Weighted Sum of Negatives," which provides the overall score for each option after accounting for the importance of each criterion.

An example of a Pugh Matrix for a product roadmap decision

The clear winner here is Option B, followed by Option C and Option A, which isn’t much better than baseline after all.

One of my clients actually recommended this matrix to a candidate who was in multiple processes and weighing up different opportunities (yea, he cares that much about his people, whether they’re already employees at the company, in his network, in an interviewing process, or otherwise 🥹).

If you want to use it for deciding against multiple offers, you can use criteria like:

  • Growth potential

  • Financial upside

  • Difficulty

  • Stress

  • Enjoyment

  • Flexibility

I think the Pugh Matrix is very similar to the Benjamin Franklin T-chart which he used to make a decision between just two options, so it was more like an advanced pros/cos framework. Here’s what good old Ben had to say about this:

My way is to divide half a sheet of paper by a line into two columns; writing over the one Pro and over the other Con. Then during three or four days’ consideration, I put down under the different heads short hints of the different motives, that at different time occur to me, for or against the measure. When I have thus got them altogether in one view, I endeavor to estimate their respective weights; and where I find two, one on each side, that seem equal, I strike them both out. If I judge some two reasons con equal to some three reasons pro, I strike out five; and thus proceeding, I find where the balance lies; and if after a day or two of further consideration, nothing new that is of importance occurs on either side, I come to a determination accordingly.”–Benjamin Franklin

I like his approach of collecting and memorializing his thoughts over a few days. You need to let stuff breathe and make space for your subconscious thoughts to catch up and surface into your conscious.

If the numbers are very obviously pointing to a single choice, then go with that. But if it’s a close call among a few, then you need to tap into your intuition.

Sit still for a moment and meditate or reflect quietly on each choice. What’s your gut telling you? Which (if any) option triggers the “full-body yes”?

Running an analysis is fun, but above all, trust your gut.

Two-Way Door

This framework was popularized by Jeff Bezos at Amazon.

It’s a way to differentiate between decisions that are consequential and irreversible (Type 1) and those that are changeable and easily reversible (Type 2) — the 2-way door that you can walk through again. It also enables fast decision-making when things fall under the Type 2 camp.

One-Way and Two-Way Door decisions

An example of a Type 2 decision is experimenting with a new product feature, e.g. adding a chat bot to a company website. If it doesn’t boost customer satisfaction as expected, it can be modified or removed with ~low cost and impact on the business. No harm, no foul.

On the other hand, an example of a Type 1 decision is acquiring another company. This has long-term strategic implications, and involves a complex integration of systems, cultures, and processes (not to mention a substantial financial investment). Once made, this decision is difficult to reverse without significant costs — and consequences. So it requires more deliberate and careful analysis vs our chat bot initiative.

The “Safe to Try” Test

This is a way to test new ideas with a bias towards action while managing risk.

It’s also how you can “walk the walk” and actually operationalize company values like ownership and risk-taking (side bar: how many companies do you know of that have spelled out or modeled what risk-taking looks like and how to do it effectively? 🤔)

With the “Safe to Try” test, you should make the decision if:

  1. It doesn’t cause a catastrophic problem

  2. It doesn’t cause any harm today

  3. You have the authority to make it


Created by Gokul Rajaram and his colleague Jeff Kolovson at Square, SPADE stands for Setting, People, Alternatives, Decide, and Explain, and it’s a framework they’ve used time and again to make difficult decisions.

Here’s a quick explainer of each:


  • What exactly are you deciding? Sometimes decisions have multiple dimensions, so you might have to keep asking this question until you get to a precise decision.

  • When? How long the decision will take and why it has to happen by a certain date.

  • Why does it matter? Context is everything.


  • There are three major roles: Responsible, Approver and Consultant.

  • Responsible — the person who ultimately makes the decision

  • Approver — the person who can veto the quality of a decision

  • Consultant — the person who gives input and feedback


  • Alternatives to the decision should be feasible, diverse, and comprehensive, and are the responsibility of…the Responsible person :)


  • Ask Consultants to share their feedback with you privately, consider it thoughtfully, then make the decision


  • Get buy-in from the Approver (regarding the decision process)

  • Walk through the decision with the Consultants

  • Ask each for their commitment to the decision out loud

  • Summarize the decision in a one-pager, and share it with the team/company

There are a ton of great resources out there to learn more about and implement SPADE. Here are the best ones:

Autonomy Ladder

This framework defines the level of autonomy and trust in a work relationship.

It has six distinct rungs, each representing a different level of independence and decision-making authority granted to an employee or a team.

Rung 1: Order-taking. At the base of the ladder, tasks are directly given and executed with no critical thought required. You simply follow instructions.

Rung 2: Investigating. Moving up, you start researching things, digesting information, and sharing your findings. You’re generally more engaged in a task or project but still rely on guidance from your Principal or manager.

Rung 3: Advising. This is when you start providing recommendations and contributing to decision-making based on your research/experience.

Rung 4: Supervised Autonomy. At this point, you just need a nod of approval before moving forward. Decision-making is mostly delegated to you, so this rung represents a significantly higher level of trust.

Rung 5: Rule-based Autonomy. You have the freedom to make decisions independently, with exceptions for high-stakes situations. This rung signifies full control and ownership over your work with few exceptions.

Rung 6: Full Autonomy. Total trust and independence without any oversight. You hear “I need help with X” and the understanding is that you will handle everything that follows.

It’s fair game to ask about the autonomy you’ll have in a Chief of Staff role during an interview. A likely response is that you’ll have varying levels of autonomy based on your Principal’s core needs, the company’s top initiatives, and as you move beyond the first 90 days.

It’s a great question to ask because you tee yourself up to highlight or re-emphasize your skills in areas critical to the role, e.g. problem-solving, strategic thinking, or the ability to operate effectively across different levels of the org.


Candidate Close-up

There is such an incredible density of talent within the Right Hand network, so to honor that, I’d like to try something new.

In addition to “Search Spotlights” where I highlight the open reqs that we’re working on for our clients, I’m going to do the reverse as well, and highlight stellar candidates (discreetly) who are looking for their next thing.

If you’re hiring and feel like the candidate showcased here could be who you need on your team, LMK! :)

🙋‍♀️ Candidate Background

This candidate was most recently a Senior Associate at a software-focused fund ($5B+ AUM). She was pivotal in the firm's early stages, joining as the first non-Managing Director (MD) hire while the firm was securing its inaugural fund.

As the sole non-MD member on a 4-person investment team, she was instrumental in closing 5 deals within 18 months, effectively operating as a standalone investment team.

She also played a significant role on the operational front, spearheading the acquisition strategy for one of their portcos where she was a board member, and successfully executing 2 acquisitions in as many months.

Before her time at this fund, she spent 3 years at a growth equity firm, focusing on sourcing and executing deals in vertical software and payments sectors, and began her career as an investment banking analyst at a major financial services firm.

💪🏻 Top 3 Skills

  • Financial modeling & analysis

  • Managing multiple priorities at once

  • Efficiency

✨ Proudest Achievement

Launching a professional podcast that focuses on women in finance and surviving 18 holes on her first-time visit to a golf course with her future in-laws.

🔥 What’s Unique

Her positivity and energy!

🎯 Career Goals

In her next role, she’d like to round out her skillset with operational expertise to prepare her for an executive-level ops or senior investment role – both areas where she believes there should be more women in senior positions. She would also like to inspire more women in the financial services / STEM / investment spaces.

Search Spotlight

Chief of Staff @ Bootstrapped CPG Startup

This CPG startup is building the next big deodorant brand in the US 😍

Founded on the principles of science-backed ingredients and customer-centric product development, our client's products offer safe, reliable, and convenient options for managing sweating and help people gain confidence and comfort in their daily lives.

The company is hiring a Chief of Staff who will be heavily focused on:

• Brand development

• Supply chain optimization

• Business operations

Ideal candidates will have 3-4 years of professional work experience and a minimum of 1-2 years of experience in operations at a CPG startup.

Additional key details:

💰 $120k+ base salary

📍 This role is remote

If you're interested and want to learn more about the company, just apply here! I’ll get back to you ASAP if your experience aligns with what they’re looking for.

Know someone who could be a fit for this role? Feel free to share this blog post!

Other Right Hand Talent searches:

Check out our job board for the full list of opportunities with our clients!

Job Opps

👗 Administrative CoS at Tory Burch Foundation - empowering women entrepreneurs

Why I don’t like it: This is a good example of what not to do when you’re hiring a Chief of Staff, namely, mis-titling the role when the person you need is a high-powered Senior Executive Assistant (and adding Administrative in front of it doesn’t help, unfortunately 🥺)

Some things a Chief of Staff should never do include:

  • Booking flights and hotels ❌

  • Managing a calendar ❌

  • Providing broad admin support ❌

The EA and Chief of Staff looking at each other :(

None of this is done with bad intention. I think people are just unfamiliar with the Chief of Staff role and that it’s meant to be a strategic hire.

Side bar → If you’re a Chief of Staff, you’re not an EA (and vice versa). If you’re an EA, you likely EITHER want to be an EA for life — and maybe shoot for more senior leveling or a specific executive to support — OR you really want a proper Chief of Staff role. Why is that? Because a Chief of Staff does strategic work, not admin.

💰 The compensation range is $34-64/hour.

📍 This role is onsite in NYC.

📥 Apply here.

👨🏻‍💻 Chief of Staff, Corporate Affairs at Kyndryl — large-scale IS

Why I like it: This role reports to the Head of Corporate Affairs, which is a unique opportunity. Kyndryl is a $5B company, so you start seeing CoS to CXO or other leaders as companies reach scale, and some even have centralized CoS functions where all the CoS report into “The” Chief of Staff.

The first line in the “Who You Are” section of the JD says that the person must work from the Manhattan office. My guess is that this means a minimum of 3x/week. A trend I’m seeing is more and more employers moving toward a hybrid 3/2 model (3 days in office, 2 days remote) and in same cases mandating 4/1 or even moving towards a full 5-days in office.

(PS — back when I was looking at CoS roles for myself in 2021, almost all were remote. Now, they are the exceptions to the rule.)

But back to the opportunity! The CoS to the Head of Corporate Affairs at Kyndryl will help manage strategic cross functional initiatives, build tools, and improve efficiency across the organization.

They need someone with a minimum of 5+ years of experience developing and delivering programs in a corporate or agency setting.

💰 Comp is $107,600 to $258,240.

📍 This role is onsite in NYC.

📥 Apply here.

🏩 Chief of Staff at Flagler Health — data-driven patient care

Why I like it: It’s an opportunity to get in on the ground floor of a seed-stage company, and their co-founder recently announced their vision of the “virtual vertical” — “a remote care platform that integrates medical providers – from physician therapist to orthopedic surgeon – into a vertically integrated health system.”

As Chief of Staff, you’ll have the opportunity to work with the CEO & COO on cross-functional projects and help facilitate comms across the org.

Ideal candidates have an analytical mindset and can use tools like SQL, Data Bricks or Excel for creating reports, are highly organized and self-motivated, and have successfully managed complex projects.

💰 Salary is $65,000-$90,000

📍 This role is remote, but living in NYC is a plus.

📥 Apply here.

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Career Coaching Session with Yuliya Mykhaylovska: Yuliya is a talent advisor to mid-career and early-career professionals. She has directly helped over 800 professionals get hired over the past decade and loves helping people find and land their dream role. She is offering one FREE coaching session to a Right Hand subscriber, redeemable in March 2024. If you’re interested in coaching, be sure you’re subscribed to this newsletter and sign up here!


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