How To Chat Friends and Slack-fluence People

Unlike many management and self-help books, Dale Carnegie classic How to Win Friends and Influence People is not about ‘hacks’ or ‘shortcuts’ but rather the fundamentals of positive and effective communication.

To be honest, I was a little disappointed about that when I first read Carnegie’s book in middle school. I thought there were going to be all sorts of shortcuts and side steps.

This is just a book about being nice?

  • “Let me repeat: The principles taught in this book will work only when they come from the heart. I am not advocating a bag of tricks. I am talking about a new way of life.”

How to Win Friends and Influence PeopleFor the past 10 years, I’ve led marketing teams at startups. Most recently, the companies I have worked with have operated large, remote crowds managed in a chat-based workspace – HipChat and Slack, respectively. I’m currently the VP of Growth at Crowdbotics, a fully remote company with employees in every corner of the globe.

In scaling these organizations, I have thought back to Carnegie more than a few times. His takeaways are simple: be clear in your communication, proactive with solutions, honest but tactful with feedback and – above all – kind. Those are marks I don’t always clear, but I try. Even upon my first read of the book as a kid, I knew that this was a more genuine, sustainable, and effective approach to leadership than any quick hack.

How to Win Friends and Influence People has aged well (though, not perfectly) and the lessons contained within are especially relevant in chat-based business environments. IRC-style chat programs such as Slack, HipChat, Microsoft Teams, Discord and RocketChat have superseded email, calls, and video chat as the primary means of internal communications for many remote organizations. Effective communication must be actively cultivated in these new mediums. It doesn’t come automatically. Effective communication practices don’t always map perfectly from a physical workspace.

With chat communication best-practices still very much evolving and coalescing, its helpful to review the fundamentals from time to time. How to Win Friends and Influence People has been in print for over 70 years, sold 30M copies, and listed as one of Time Magazine’s ‘most influential books of all time.’ Most people are already familiar with the book. In fact, the sections within are not so much lessons, but rather helpful reminders. The has book staying-power because it focuses on the basics.

Below are some practical examples of how you can apply the principles from How To Win Friends And Influence People for more effective chat-based business communication.


Don’t criticize, condemn or complain.

It’s human nature to not like to admit when we are at fault. When criticized, most people become defensive and resent their critic.

  • “Instead of condemning people, let’s try to understand them. Let’s try to figure out why they do what they do. That’s a lot more profitable and intriguing than criticism; and it breeds sympathy, tolerance and kindness. “To know all is to forgive all.”

Much can be lost between the lines with text. At times, communicating complex ideas via chat can be frustrating. Always assume positive intent in others. Respect their expertise, work ethic, and and give them the benefit of the doubt.

Be patient and proactive. When noting an issue that needs to be addressed, either suggest a solution or suggest how a solution might be arrived at. Maintain a “yes” mentality. Address problems, rather than labeling individuals.

Give honest and sincere appreciation.

Appreciation is surprisingly powerful. While criticism often saps from an individual’s maximum potential, honest appreciation can bring out their best. To be well-received, appreciation must be sincere.

  • “She noticed that occasionally he did a particularly good piece of work. She made a point to praise him for it in front of the other people. Each day the job he did all around got better, and pretty soon he started doing all his work efficiently. Now he does an excellent job and other people give him appreciation and recognition.”

Create a dedicated #shout-outs channel to show recognition. Highlight specific achievements, even if small.

But, don’t stop there.

Share appreciation with individuals directly in DMs. Share it in your regular departmental channels. Surface it in larger groups, when appropriate. Both ‘public’ and ‘private’ appreciation have their places. Reinforce specific positive outcomes in the moment.

Look for opportunities to do this each day. Make it part of your routine.

Say “thank you” often.

Highlight praise from a nested thread in the main feed, just as you would some other key point, to underscore your recognition of their improvement, achievement, or initiative.

Arouse in the other person an eager want.

To get something out of another person, first forget about yourself, and see things from their point of view. Look for the common denominator in your objective. Your wants must be in alignment.

  • “The only way to influence people is to talk in terms of what the other person wants.”

The most straightforward way to understand another person’s wants in a business setting is to articulate shared goals.

Start by creating a shared document for objectives and key initiatives. Quarterly OKRs are an effective system, but you can choose a format that fits best for you organization.

A shared goal-setting documents should include:

  • Objectives – What do we want to achieve in given time-window?
  • Key Initiatives – What specific programs will be worked on to support each objective, by who?
  • Metrics – How are we quantifying, qualifying, and tracking success?

In most cases, individual objectives should originate from departmental goals. Departmental goals should originate from company goals lead by executives or the board.

Key initiatives will often involve multiple stakeholders, and can be broken down into phases of planning and execution.

Once you have reports established your goals, automate updates at regular intervals in relevant channels. Most MAS, CRMs, analytics tools, and dashboard have an out-of-the-box Slack integration. You can also use Zapier to trigger a reminders. At a minimum, you can use Slack’s native reminders to resurface the report link at regular intervals.

Offer suggestions. Invite suggestions. Get people involved in the decision-making process.

Become genuinely interested in other people.

The most effective way to make lasting friendships or business relationships is to be genuinely interested in the other individual.

  • “I have discovered from personal experience that one can win the attention and time and cooperation of even the most sought-after people by becoming genuinely interested in them. “

Chat-based communication can sometimes feel one-dimensional in terms of social interaction, but it doesn’t have to.

Ask people how they’re doing. Ask them what they’ve been up to.

Working by oneself at home — or even in a co-workspace — can be isolating. Unless you make it priority, it can be easy to neglect to make and maintain connections with co-workers .

Take a minute to see what co-workers with whom you collaborate closely are broadcasting on public social media. There is, of course, a line on social between what is meant for friends and family vs. co-workers – and what topics are work-appropriate – but you should be able to discern one from the other with reasonable judgment.

Are they into drone racing, rock-climbing, coaching little league, local theatre, The Office_?_

Ask them about it.

Smile

Facial expressions can be as important to communication as the content of a message.

  • “Your smile is a messenger of your good will. Your smile brightens the lives of all who see it”

Some skeptics still eye-roll about the use of emojis in business conversations – and of course it can be overdone, or not done well – but the impact of an emoji is undeniable.

Emojis have an amazing ability to change the tenor of a chat exchange.

For many people, it’s even easier to wear a smile in text than in the real world. In chat, it’s a matter of choice. Emoji’s are free.

Remember that a person’s name is to that person the sweetest and most important sound in any language.

People love the sound of their own name.

  • “Jim Farley discovered early in life that the average person is more interested in his or her own name than in all the other names on earth put together. Remember that name and call it easily, and you have paid a subtle and very effective compliment. But forget it or misspell it — and you have placed yourself at a sharp disadvantage.”

In chat, you have the ability to summon people (or not) with an @-mention. Use that power wisely.

Put some thought into when to use an @-mention, “CC”, or just simply use a name in sentence.

The tone and urgency of a message can be received quite differently by the use of a name

  • Did the email go out?
  • @Jess, did the email go out.
  • Hey Jess, did the email go out?
  • Did the email go out? CC @jess
  • Did the email out. @jess

There are not firm and fast rules to apply here. Just be conscious of use.

Make every effort not misspell a name. If you do, correct it.

Do not use non-specific pronouns when you need assistance. People assume others will take the task, so don’t leave request open-end. Don’t ask “Can someone do X?” Assign your request to a specific person. Otherwise, it may not get done. Don’t be afraid of asking others for help.

Be a good listener. Encourage others to talk about themselves.

Good conversation is about give and take. Listening is as important as conveying ideas. More often than not, people want to be listened to more than they want to be informed — especially in a business-context.

  • “So if you aspire to be a good conversationalist, be an attentive listener. To be interesting, be interested. Ask questions that other persons will enjoy answering. Encourage them to talk about themselves and their accomplishments.”

How can you be a good listener on slack?

The best way to be a good ‘listener’ on Slack is to be a good ‘asker’.

  • Are there any obstacles I can remove for you?
  • What aspects of your work would you like more or less direction from me?
  • What can I do better or differently as your manager to support you?
  • How might I make this project more challenging or interesting for you?
  • If you were me, what changes would you make?
  • Are there any events or training you’d like to attend to help you grow your skills?
  • Are there any projects you’d really like to work on if you were given the opportunity?
  • What skills do you have that you think are underutilized?
  • What skills would you like to develop right now?
  • What issues are we most likely to run into?
  • Can you share some of the details around that particular issue? (Who was involved? Where? When? For how long?)
  • Who is doing a great job on the team right now?
  • What were your biggest time wasters or roadblocks last week?

Here is a large list 1:1 questions you can apply in the course of regular communication

Talk in terms of the other person’s interests.

If you talk to people about their interests, they will feel validated and value you in return.

  • “Talking in terms of the other person’s interests pays off for both parties.”

[See ‘Be A Good Listener’ and ‘Be Genuinely Interested’]

Don’t underestimate #random. In between the memes, the #random channel is often where people share what is truly most important to them.

This could be a work-related idea, such as an article they think the team may benefit from, or perhaps highlights a concept they think is currently being overlooked in to org. Sometimes it’s something they’re proud of: their kids, their backyard, something they baked, a blog post a friend of theirs wrote.

Even something as simple as a meme, is a window into how people tick. #random may be the most underrated channel in your workspace. Everything shared there was done so for a reason, and had no other place to find expression.

Make the other person feel important – and do it sincerely.

The Golden Rule is the principle of treating others as you want to be treated. It is an ethic of reciprocity found in many cultures.

We each want to feel valued and important. A simple way to make others feel valued is to communicate their worth by expressing your appreciation for them.

  • “Let’s try to figure out the other person’s good points. Then forget flattery. Give honest, sincere appreciation. ”
  • “Every man I meet is my superior in some way. In that, I learn of him.”

There are many ways to make someone feel valued.

  • Communicate that their work is making an impact.
  • Ask for their expertise.
  • Show them the positive impact of their work.

The Golden Rule can also be framed as a prohibition: Do not treat others in ways that you would not like to be treated.

Do not,

  • Neglect to follow up with their threads. – Set reminders to follow up with threads if you don’t have time time the moment
  • Offer short, ambiguous, open-end responses. – Provide adequate responses to questions.
  • @-mention individuals or @channel when you don’t need their attention – Show respect for others’ attention.
  • Don’t read through what they type out. – If someone takes the time to type it out, read it. (If it’s consistently too much for you to read, address that. Don’t ignore the issue or the individual)
  • Be passive aggressive – It reads just as clearly in chat as it does person-to-person

Win people to your way of thinking

The only way to get the best of an argument is to avoid it.

You can never really win an argument. The other party will either feel diminished or seek to bolster their own position. Avoid arguments.

  • “Distrust your first instinctive impression. Our first natural reaction in a disagreeable situation is to be defensive. Be careful. Keep calm and watch out for your first reaction. It may be you at your worst, not your best.”
  • “Look for areas of agreement. When you have heard your opponents out, dwell first on the points and areas on which you agree.”

Avoid arguments, especially in public channels.

If not possible to avoid a disagreement, or you need to work through a potentially contentious issue, take the conversation to direct message. Negative feedback should be relayed in 1:1s.

The asynchronous nature of Slack also makes it possible to ‘put a pin’ in discussions. More often than not, both parties will have a fresh perspective and less emotional attachment to the issue once revisited.

When you take a disagreement ‘offline’, make sure some resolution is eventually reached. Don’t just bury the question. Doing so is likely to create further misalignment or blockers.

If the disagreement originated in a channel, it can be valuable to circle back to the channel with a summary of the solution.

Articulate that you understand a person’s position and priorities.

Show respect for the other person’s opinions. Never say, “You’re wrong.”

Telling people they are wrong puts up a wall. It only serves to offend the other party and insult their pride. You can be honest without being curt.

  • “We sometimes find ourselves changing our minds without any resistance or heavy emotion, but if we are told we are wrong, we resent the imputation and harden our hearts.”

There are always more effective ways to communicate in a disagreement than telling people they are wrong.

  • “Here are the numbers I’m seeing.”
  • “How are you accounting for X”
  • “X was a similar case of this in past, with Y results.”

Not only does “you’re wrong” get people on their heels, it distances everyone from a solution.

“You’re wrong” is a solution-stopper. It is especially important to avoid burying issues in chat because the discrepancy may not be revisited until it as surfaces as a much larger later on.

If you are wrong, admit it quickly and emphatically.

When wrong, admit it quickly. Not admitting when you are wrong diminishes trust.

  • “When we are right, let’s try to win people gently and tactfully to our way of thinking, and when we are wrong — and that will be surprisingly often, if we are honest with ourselves — let’s admit our mistakes quickly and with enthusiasm. Not only will that technique produce astonishing results; but, believe it or not, it is a lot more fun, under the circumstances, than trying to defend oneself.”

Beyond the general application of this principal, a common scenario in chat-based communication is misinterpretation of a message.

We’ve all had the experience of mis-reading a message or mis-ascribing intention or tone to a message.

Here are some additional helpful tips for remote collaboration best practices.

Begin in a friendly way.

If you begin interactions with others in a friendly way, they will be more receptive.

  • “The sun can make you take off your coat more quickly than the wind; and kindliness, the friendly approach and appreciation can make people change their minds more readily than all the bluster and storming in the world.”

Consider your own initial reaction to two different responses to the the greeting, “How’s it’s going?”

  • “Oh, you know. OK, I guess. It’s going.”
  • “Going great. How are you? 🙂 ”

Which gives more a positive impression?

You don’t have to lay it on thick, or be disingenuous. Both greetings are initiated by reflex more than anything to do with your mood. Choose to set your default to positive. The opening to a conversation sets the tone for everything to follow.

Approach challenges with a ‘yes’ mentality: ‘there are solutions, and we will find them.’

Be especially conscious of how your communications may be perceived. Take time to re-read your messages and edit for clarity.

Call attention to people’s mistakes indirectly.

No one likes to make mistakes, especially in front of others. Scolding and blaming only serve to humiliate. If we subtly and indirectly show people mistakes, they will appreciate us and be more likely to improve.

  • “Calling attention to one’s mistakes indirectly works wonders with sensitive people who may resent bitterly any direct criticism.”

Initiate constructive criticisms in direct messages.

Even if the feedback is valuable to the others in a group, a channel as a whole, first relay that information in private.

A complaint will always be better received (and addressed) if it is framed as an opportunity for improvement accompanied by specific suggestions.

Talk about your own mistakes before criticizing the other person. When something goes wrong, taking responsibility can help win others to your side.

Nothing diminishes the dignity of an individual like an insult to their pride. Allow people to save face and they will be motivated to do better in the future and confident that they can.

Give individuals — and the team — a great reputation to live up to, they will desire to embody the characteristics ascribed to them.

Good work!


Remote work has been on the rise for years now, and is becoming the preferred method for building effective global teams, not a novelty or a compromise. Whether you’re building a remote-first organization, or making adjustments to a new remote-work cadence, you can find a list of additional remote work management resources here. With the right tools, operations, communications, and attitude, remote work organizations have the ability not only to achieve the same effectiveness of traditional physical work environment, but exceed them.

2019 Reading Recap & Recommendations

For a few years now, a former colleague — an author and known book-hoarder — has suggested insisted I post an end-of-year reading re-cap. I promised to do so this year.

Here are the books I read in 2019, in the order I started them:

Here are a few 2020 book recommendations from this list:

The Tangled Tree – David Quammen

Most people are probably not familiar with Horizontal Gene Transfer (HGT) and, accordingly, may possess a slightly outmoded understanding of evolution. The Tangled Tree is a good introduction to HGT. David Quammen is one of my favorite nature writers, and I would recommenced his other books as well. (Quammen’s short story collection, The Boilerplate Rhino, is a good place to start.) The academic history of evolutionary thinking is quite interesting. The near future of biology — inevitably to impacted by the operationalization of genetic editing via CRISPR — is sure to be even more so.

No One Is Too Small To Make A Difference – Great Thunburg

She was on the cover of Time Magazine. She was nominated for a Nobel Peace Prize. I was walking though San Francisco last week and saw her face 40-feet tall on the side of a building. Worldwide, people know the name “Greta,” and they didn’t last year. This short collection of her speeches is worth reading because it is perfectly of-the-time.

To better understand the facts, assumptions, and projections tied to the oft-referenced 1.5°C warming threshold, I suggest also reading the 20-page “Summary for Policymakers” section of the “IPCC Special Report on Climate Change”, which has set the tone for the broader discussion on climate change.

The Patch – John McPhee

John McPhee is one of my favorite non-fiction writers (and even tops the aforementioned David Quammen as one my favorite nature writers). What I love about this collection of previously unpublished snippets from McPhee is what I love about reading shorter bits by EB White. McPhee, known for his sprawling essays, is just as compelling in unpolished bits and bites. If you’re new to McPhee, I would recommend starting by first sampling a collection like The John McPhee Reader, or a single notable essay like “Atachafalya,” then eventually working you way back to The Patch, but The Patch was probably the book I enjoyed reading most in 2019.

The Metropolitan Man – Alexander Wales

People think I’m joking when I say that Harry Potter rationalist fan fiction is more enjoyable than the original. They also typically don’t take me up on reading recommendations a hundred thousand words longer than War and Peace. I tell the I-don’t-like-reading-on-a-screen crowd that their issue can be solved for as well, but it doesn’t seem to matter. For those who don’t want to commit several dozen hours to reading Yudkowsky — or reading at all, for that matter — The Metropolitan Man audio is now available for free via The Methods of Rationality podcast. It’s similarly entertaining and thought-provoking, clocking in at only 7 hours long.

Journal Of A Trapper – Osbourne Russell

Russell is a name you’ll hear less than Coulter, Lewis, Clark, or Jackson, but his first person account of 8 years as a trapper in frontier Yellowstone-country is as compelling as any other account. The edition I read was shaped like a giant floppy workbook with tiny print which added some additional novelty value to the read.

Open Office Hours

I’ve had a handful of recent requests to have ‘office hours’ to discuss startup- and marketing-related questions.

I blocked off some Tuesday afternoons PST where you can book a short call. These office hours are open to anyone.

If you’re in one of the groups I’m working with in either the StEP Entrepreneurship Program or HaaS MBA Growth Hacking class at UC Berkeley, just email me directly.

I will keep this window open as long as my schedule allows. (I may shift the time, in which case you’ll see the updated times on Calendly. If no times are available, they have been booked.)

I’ll keep this time open for as long as practical. My hope is that the format works out, and I can keep the window open for some time.

Thanks. I look forward to chatting.

You can book open office hours here.

An Album A Day (Year 2)

Last March, I began listening to a different album every day. Here are a few thoughts on the exercise and along with my favorite albums from year two.

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When I discussed with people that I was listening to a new album a day, the most common question was, not ‘why’ but rather ‘how do you pick them?’ Most everyone seemed to readily see value in the exercise, though I don't know if everyone would agree on what actually makes something like this worthwhile.

Here's how I chose albums to listen to.

Read more