Use AI to do Just One Job

~ Sasha ~ 1 Comment

Are you curious about AI but still a bit skeptical?  Then this post is for you.

First, a test: Have you found at least one important task that you can now do better or faster thanks to AI?

Yes! Hooray.

No? Keep reading.

To put the “no” into context, you are, in effect, making an active choice not to use a major productivity enhancer. It’s like insisting to do your calculations by hand instead of Excel, or writing by hand instead of using Word or Google docs.

If that choice is essential to your creative process, then I encourage you to stick with it.

But there is definitely somewhere that you should be using AI.

If you’re not using AI, you may have read about it or tried ChatGPT, but it’s not part of your daily workflow.

The road from here to there is short, just follow these steps:

  1. Pick a task that you do often, that you understand well, and for which you are a good judge of what good quality looks like.
  2. Log in to one of the new AI models. I would suggest you pick ChatGPT-4 (free) or Claude 3 Opus (I pay $20/month for this).
  3. Play around for 1-2 hours, working to get the AI to help you do your chosen task.

A mindset shift around AI might help, and what helped me the most was this How Should I Be Using AI Right Now podcast by Ezra Klein.

My takeaways from the podcast were:

  • Anthropomorphize the AI. Think of it like a person you’re working with, not like a computer. More specifically, think of the AI like an intern who’s a couple of years out of college who is very capable but who needs (and is open to) a lot of feedback.
  • Tell the AI who it is / who you want it to be. Meaning, give it a personality. Tell it to be Steve Jobs, or tell it the characteristics of your college advisor or best friend or editor. When you tell the AI what personality to have, it responds with the right tone and syntax and, more surprisingly, you are changing the quality of the responses.
  • Give the AI examples of what ‘good’ looks like. Share examples of the work product that meets the standard you want the AI to hit. Better yet, share 10 of those. I find copy/pasting text the easiest way to do this. Explain what each example is and how representative it is of the generalized output you’d like to see. The more you can share, the better.
  • Give the AI tons of feedback on its output. This is where the “helpful intern” mindset helps. The AI needs to be told what to do, so tell it! Here are some examples from when I was playing with teaching the AI to write a good follow-up email from a sales call. (aside: the AI is reading what I write to decide how it will write. So I’m intentional about writing like I write.)
    • “It’s pretty good. The opening is a bit generic and I’m always trying to avoid more general statements, so please tone that down a bit and stick to specifics.”
    • “You’re getting there. Let’s leave that as a placeholder for now. It’s a good start for the more standard emails that I write. But sometimes I’m more open ended.”
    • “OK a few things – avoid unnecessary modifiers like “truly believe” and try to avoid repeating words (you used “believe” twice at the start of two paragraphs).”
    • “This sentence is terrible ‘Bringing together diverse perspectives and expertise will be critical in unlocking innovative solutions.’ It is a statement full of platitudes. Avoid writing like this always.”
    • “Yup. Better. But this sentence is still full of platitudes. ‘and have been impressed by the insights and leadership you’ve brought to the space.’ What would be better is either to delete it or to find something relevant to refer to that is more specific. Also on the prior example, ‘exciting opportunity’ is breathy and doesn’t need the word ‘exciting.’ Don’t be afraid to be direct and not too flowery.”
    • It finally produced something decent, so I wrote, ‘Good. This works as a point of reference, stylistically.’ I named that style so I could refer back to it in the future.

I expect you’re getting the feel for this…I gave more feedback on various iterations, either at the general level (“that is waaaay too wordy. Try again but cut 80% of the words”) or much more specific (“This sentence is terrible, the whole second half of it is a word salad that adds no value.”). Again, the mindset of “I’m talking to an intern” really helped me stick with it here.

After about an hour of this back-and-forth, the AI was giving me what I wanted at a high standard, and this standard got me an 80% first draft that will save me tons of time.

In addition, working on a real task—one that is important, and where I have domain expertise—helps me learn about what the AI can and cannot do well.

And the impact of that is huge. It’s like crossing a threshold as I imagine the amount of leverage each of the 120 people on my team could have if this becomes part of their workflow. What if each person could have a “very helpful and eager intern” at their beck and call? Imagine the impact of that, and add to it the operational stack that we can hack to pieces with the aid of this technology.

I hope this is the post that nudges you to take another shot at this, and that, in a weeks’ time, you’ll have played with and succeeded at getting AI to do SOMETHING meaningfully helpful in your professional or personal life.

If you need more ideas of where to start, here they are:

  • Writing your professional bio
  • Creating meeting summaries
  • Writing follow-up emails from sales calls
  • Resume screening to avoid bias
  • Creating a negotiation training module
  • Helping you prioritize your to do list
  • Summarize this data set
  • etc. etc.

Don’t forget: the assisted here is the point.

I generated that list with help from AI.

It gave me two lists of 10 ideas. All of them were too wordy. I liked 5 of the ideas, and I made those 5 better, added links, and I added two of my own

Voila.

(p.s. more On Interviewing Well posts are in the queue. Stay tuned.)

On Interviewing Well: Convey Deep Self Knowledge (3-3-2)

~ Sasha ~ 1 Comment

What is the person interviewing you trying to accomplish?

We know what they are doing: posing a series of questions with the ostensible goal of figuring out who you are, what your strengths and weaknesses are, and how well you’ll fit culturally within their organization.

Knowing that, you have a choice.

Your first option is to play their game and answer every question as well as you can. When you do this, you are, bit by bit, handing them puzzle pieces that make up the picture of who you are. Your hope is that those pieces are accurate and complete enough that the picture they paint is a reasonable representation of you and of you in this job.

Unfortunately, this approach is flawed. First, it assumes the interviewer will ask enough questions, and the right ones, so they’ll end up with a good-enough set of “you” puzzle pieces—that’s leaving a lot up to chance. Worse, you’re setting yourself up to be compared in a like-to-like way with everyone else who answered that same set of questions.

Here’s a second option, inspired by the most creative interviewing I’ve ever seen. The interviewer had a list of 40 traits (e.g., data analysis, public speaking, sales, making new connections, coding), and she told the interviewee that she’d be reading down that list. She asked the interviewee to to rate their abilities on each trait on a 1 to 10 scale. She would go through the list quickly—the whole thing probably took two minutes—and then discuss.

So much is happening here. The interviewee quickly figures out there’s no gaming this system: they can’t credibly say they’re great at everything, so they are likely giving a more accurate picture. Plus, so much information comes across about the candidate beyond each individual answer: are they a tough or kind self-grader? How quickly do they answer on some traits (I’m confident about this) vs. others? How consistent are the answers? What does the overall picture look like? And how do they react to this surprising exercise?

Since most interviewers won’t take this approach, your option is to take it for them with the 3-3-2 approach.

With this approach, you are going to describe eight things about yourself:

Three that you’re solid at

Two that are weaknesses of yours—things that, if they’re core to this job, mean that this job isn’t right for you

And three things that are your superpowers

For example:

“Three things that I’m good at and would be a core part of any job I’d do well: managing large teams, handling stress/complexity, and selling.

On the other hand, two things that I’m really not great at are: creating PPTs to present my ideas; and living and dying by getting the last decimal point right. I’m good at details, but if that’s my whole job I’ll go insane.

And my three superpowers are: strategic thinking (figuring out the way forward from a bunch of complex options), coaching, and building community.

I’d be happy to give you examples of any of these if that would be helpful.”

You have to be really honest here—no “the thing I’m worst at is having high standards.” You’re intentionally stepping outside of the interview game and telling the interviewer what she really wants to know.

What’s powerful about this is the clarity and confidence you demonstrate by giving someone all the pieces to your puzzle. You’re saying “this is me, the whole story, both the good and the bad. If that’s a fit for what you’re looking for, great. And if it isn’t, that’s fine too.”

Of course, you can adjust as you see fit: how deep are you going to go with what you share? How long a list?

What matters most is that it’s genuine: you’re communicating that you’ve reflected deeply on yourself. You’re saying that you understand this is a matching game, not a “pick the best candidate” game. And you’re giving yourself the chance to say, without bragging, “out of everything you might be looking for, these are the areas where I really shine.”

This approach consciously rejects the cat-and-mouse game of interviewer question and answer. It demonstrates the kind of self-knowledge that itself will distinguish you from the pack.

Most of all, it’s breaking the mold, doing something memorable that says “I’m an open book, this is the information we both need to proceed. Let’s have that conversation.”

Other posts in this Series:

On Interviewing Well: Introduction

On Interviewing Well

~ Sasha ~ 2 Comments

I’ve had several conversations recently about how to interview well.

These conversations reflect an innate understanding that we’ll never stand out just by answering questions better—we have to get above the fray.

With that framing in mind, I will be writing a series of posts on this topic.

These posts will likely be most relevant for people later in their careers looking to land more senior roles. But hopefully the themes and approaches will be useful to everyone.

The topics will include:

  • How to convey deep self-knowledge
  • What interviewing has to do with sales and with dating
  • Being clear and unwavering about intention
  • The truth behind “informational meetings” (and how to 100x your odds in getting a job)
  • The transformation from interviewee to partner.

The focus of these posts will be on how you shift the conversation. If the game you’re playing is trying to be the “best” out of 50 or 500 applicants, that is a loser’s game—the odds are stacked too high against you.

Instead, your objective is to show up as a completely different kind of candidate, and to push the person hiring into a yes/no decision about whether to hire someone like you. When you do that, you’ve moved from 1 in 500 (“trying to be the best in a big crowd”) to 1 in 2 odds (“do I want to hire this unique, surprising person for this role?”).

In the process of standing out, you’re going to do more than increase your odds. You’re going to discover whether the organization that’s hiring wants someone different.

Because if they don’t want that, then you probably don’t want them.

Stay tuned, and feel free to share the series with someone who will find it helpful.

Share Your Strategy with Everyone

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We sometimes get protective about our strategy, like a cat we don’t want to let out of the bag.

When asked, “What’s new?” we answer with vague pleasantries rather than cutting to the quick of what’s on our mind.

This fear is misplaced because our understanding of whatever we are grappling with is 100x more granular than that of the person we’re talking to. We also have the people, brand, and momentum to take our strategy forward.

Instead, we should actively choose to share meaningfully with the people we meet. This leads to a genuine discussion at a strategic level, which:

  1. Deepens engagement and trust
  2. (If we listen closely) Allows the other person to share a story or insight that could catapult us to the next level of clarity.

This kind of deep, open conversation stays with someone. By talking at an honest, strategic level, we invite them to our side of the table. If the conversation is both engaging and memorable, they’ll keep thinking about to for weeks or more, becoming a powerful ally.

And, by telling a vivid enough story about our strategic dilemmas, we offer an opportunity for engagement, so people can dig through their own deep experience to find the perfect vignette with the diamond of wisdom just for us.

As Tom Peters said, “innovation comes only from readily and seamlessly sharing information rather than hoarding it.”

Telling our story well and sharing openly brings together more allies, horsepower, and willingness to take that story to new heights.

The Inefficiency is the Point

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My 13-year-old daughter has been working her way through writing 75 thank you notes for the too-generous gifts she received for her Bat Mitzvah.

Note by note, one at a time, in the mix of cursive and print that is the hallmark of an early teen.

If she really concentrates, she might be able to 5 or 6 of them in one long sitting.

So much of our professional time is spent finding the last 10% of efficiency: the hacks, the shortcuts, the things we can strip away.

And, indeed, “frictionless” is valuable most of the time.

But, unless (and even if) you are running a fully scalable, 1000x software company, what’s going to make the difference, and what’s going to make them remember you, isn’t (just) how hassle-free it was.

What they’ll remember are the personal touches.

The effort that shows through.

The smudges.

The corrections.

The imperfections.

The one-of-a-kind patina that shows that you really, truly care.

Frantic

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When the stakes get really high, we have to know how to be…

…urgent

…focused

…super-diligent

…fast

…top priority

…and now!

All of those are fine. Sometimes we need to sprint. The unexpected can and does come up, and we have to be calm under that pressure while hitting our top gear. There are few greater differentiators than the ability to deliver our best work quickly and under pressure.

But frantic is something else entirely.

Frantic communicates anxiety and fear.

Frantic puts everyone on their back foot.

Frantic says “we’re in big trouble” and activates the amygdala.

In that reactive place, we cannot produce our best work, and our bonds to one another weaken. It’s a terrible place to be.

Think about it: at the end of a sprint, we might feel exhausted, but we’re also proud.

And at the end of a sprint that we did together, we feel closer to one another.

Whereas at the end of frantic, we just feel relief that it’s over, and we hope that it will never happen again.

If you’re in a position of authority, no matter what the context, you can never be frantic, and you can never communicate frantic to your team.

Period.

 

What Gets Measured Doesn’t (Necessarily) Get Managed

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There’s an old adage that “what gets measured gets managed.”

The choice of what to measure, the thinking goes, is itself an act of prioritization: since this is important enough to measure, we’re going to pay attention to it. And that will create a reinforcing feedback loop.

The problem is, in a world with a proliferation of data, the old adage no longer holds.

So much is getting measured that the act of measuring itself is insufficient. Tons of things are getting measured that are not getting managed.

What we need now is more than measurement: measurement PLUS attention, focus, and inquiry.

It’s simple, actually: to raise something in priority, we must regularly look at the numbers, inquire about why they did or did not change, get a feel for them and regularly insert them into conversation.

Otherwise they just sit there, inert, at best serving as a warning light when things get way off track.

But by then its too late.

Here’s a quick test. Do you know:

  1. What the 5 most important numbers are for your organization?
  2. What the 3 most important numbers are for each function?

On the second one, the only way to really say “yes” is:

  • Am I looking at these numbers a few times a week?
  • Am I discussing them with my team, and with my boss?
  • Does this regular inquiry lead to concrete action?

Only this level of engagement transforms data into a management tool. Only this level of engagement evolves into intuition about what these numbers mean, what makes them move the way you want them to move, and whether they’re the right numbers at all for running your organization.

Self and Role

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There’s a tightrope we all need to walk in our professional relationships, the balance between self and role.

One of the greatest joys of my professional life is that I’ve found a career that allows me to work with so many great people. Folks who are committed to social change are, in my experience, more likely to be their whole selves in a professional environment, and this makes it more common to develop strong relationships with our colleagues.

This is a plus, but it creates something delicate: learning to be in relationship both as our selves and as our roles.

Because sometimes there is a virtuous, reinforcing loop between our strong personal and professional relationships: great friends find it easy to fill in the blanks for each other and have each others’ backs. We have a deep foundation of trust to draw upon, one that gives us more latitude and more leeway.

But sometimes these forces pull in opposite directions. We disagree about something, or one person has to make a tough call that affects the other. Or, harder still, we need to have a difficult professional conversation that could create strain in our personal relationship.

What we must remember is that it’s our obligation to push to this uncomfortable place—especially if our shared work is in service of others. We must be willing to take on relational risk, to prioritize the conversations we need to have as professionals even if this might weaken our personal relationship for a period of time.

To make this possible, both people need to be committed to, and adept at, switching hats—to know that sometimes we’re talking as friends, and sometimes we’re talking as colleagues, and there are days when these cannot be the same things.

And, the hard fact is that, the more senior you get, the harder it gets to take “role” hat off, even if you’d like to.

That doesn’t mean that you can’t have strong friendships and relationships at work, it just means that your role has become important enough in your organization that you occupy it for others no matter what.

 

The Opening

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We all come across these moments in our careers: something shifts, and suddenly we find ourselves in a bigger role than the one we signed up for.

That “something” that changed could be many things, but the most common is someone who was senior to us quitting or taking on a new role.

This shift creates an opening.

And the question is: what are we going to do with it?

We’ve known for a while that we could play bigger, that we don’t feel as seen as we want to, that we are a bundle of as-yet-unrealized potential.

At the same time, we must fight our natural sense of inertia—the object that we are tends to stay in motion in the direction it has been heading—and we carry with us, always, a dollop of fear.

The Opening moment is the perfect chance to do away with all of this: a gap not of our making has appeared, and the downside to stepping up is almost zero.

So why not take a swing? Why not you? Why not now?

Quietly, there are lots of people rooting for you, lots of people who believe in you, people who know you are ready for the next thing.

This is what opportunity looks like.

Go ahead and grab it.

 

The One Non-Negotiable Trait of Great Team Leaders

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At a workshop I facilitated a few weeks ago, we asked everyone to share, in small groups, the characteristics of the most effective leader they had ever worked with.

The most common behavior they mentioned was: this is someone who always has my back.

It makes sense, and aligns with Reed Hastings’ / Netflix ideas about how to think about our working relationships: we are not a family, we are a high-performing sports team. From the Netflix Culture page:

A family is about unconditional love. A dream team is about pushing yourself to be the best possible teammate, caring intensely about your team, and knowing that you may not be on the team forever. Dream teams are about performance, not seniority or tenure. It is up to the manager to ensure that every player is amazing at their position, plays effectively with others and is given new opportunities to develop. That’s how we keep winning the championship (entertaining the world). Unlike a sports team, as Netflix grows, the number of players also grows. We work to foster players from the development leagues so they can become the stars of tomorrow.

The best teammates, and the best bosses, are the ones who make you better, the ones you can rely on, the ones that will back you up if someone comes after you and catch you if you fall.

The story could end here, but it doesn’t.

Back at the workshop, we moved from small breakout groups to the full group.

In the report out, the “someone who has my back” headline subtly got transformed into “someone who protects their team,” and not everyone noticed at first how different these two things were.

Yes, great leaders protect—give cover to—their teams. But that is hardly enough.

“Protection” and “having your back” are not the same thing.

When I have your back, that means that I am there to support you, to be your advocate, to ensure that you are operating in a context where you can always succeed.

And that also means that, in private, I am telling you the hard truths, sharing where I think you have more to give, expressing to you what I know is possible for you and for us. I’m a coach, to be sure, and I’m one who tells you the whole story.

That’s a much broader remit than someone who only protects her team. Someone whose headline is “protection” is prioritizing safety and may be shying away from productive conflict and from the messages that need, over time, to be heard.

You can see this distinction play out in Google’s lessons from how to create great teams, based on research they conducted over two years looking at 180 teams.

The five characteristics Google identified as mattering the most were:

  1. Dependability: I talked about this in Teamwork, partnership, culture, and passing the ball
  2. Structure and clarity: well defined roles and goals
  3. Meaning: “the work has personal significance to each member”
  4. Impact: “the group believes their work is purposeful and positively impacts the greater good.”
  5. Psychological Safety: “A situation in which everyone is safe to take risks…A culture where managers provide air cover and create safe zones so employees can let down their guard.”

Someone who protects their team is likely providing psychological safety, and that’s important enough that it makes the Top 5 list. But limiting ourselves to “protecting” team members means we’re playing a narrow role, one in which we’re more likely to see ourselves as a filter or a buffer between what we see and what they see.

That’s certainly helpful some of the time: when a team member lacks confidence in certain tasks; when they are newer; when the team is forming and the bonds between folks, and the resilience of the team as a whole, is low.

But in the long run, protection alone is not enough.

We have each other’s back by buffering sometimes, filtering others, but, also, by providing real clarity of role and expectation, of potential, of upside.

And, most of all, we have each other’s back by communicating our clear conviction that we know this person can be great, and that we will walk with them down the path to greatness.