This is the blog post version of my talk with Amy Martin, Project Manager, SF Digital Services, on April 22, 2023, at BSides San Francisco. Video to come. Slides are here.
Every security initiative has two sides. One is purely technical: we need to prevent abusive emails from getting into company inboxes with a product, or we need a code scanner built into CI/CD to look for common insecure patterns in new pull requests. All of these, even those that seem purely like a matter of automation once they’re set up, also have a second side: the people involved.
We’ve both dealt with the human side of implementing security-related processes. Breanne has grappled with it as a site reliability engineer working to refine IAM roles and as a security engineer creating and refining processes around evaluating and approving Chrome extensions and GitHub Actions. Amy has encountered it while pushing technical advances needed to get ahead of software EOL dates and standardize CMS usage among teams who depended on stability to do their jobs. Both of us have learned the value of creating change through policy and process without making everyone hate you.
To that end, we’re using the term users a little differently than usual. Often, this refers to end users, people using your company’s product, the public, or anyone on the outside who needs what we create. What we’re discussing here certainly affects them too, but our focus here is on internal users: partners within our organization, people who depend on our work to get their work done, and people who need to buy into what we’re doing in order to make a better, more secure experience for them and everyone else. Without them, no security transformation will ever truly work.
Two failures, and hope
In January 2022, Amy left her public library job and joined the Delivery team at San Francisco Digital Services. They needed to move about 80 websites off their Drupal 7 platform and onto SF.gov, the City’s unified and accessible website, in advance of the planned end of life of Drupal 7. That was meant to be in November 2022 and did not happen, but that’s another story.
When Amy started at Digital Services in January, about a third of these departments didn’t know yet that they had to move their website by November, and many of them liked their current, government-speak oriented websites just fine. SF.gov is built for usability and accessibility, and plain language is key—not government speak. Every site they moved required content redesign, and Department staff had to be trained to do the work
How can government Digital Service staff convince civil servants and other agencies to embrace digital transformation in the face of a big unwanted project?
The short answer is that they only did part of that. They moved the websites before their deadline, and they got people started on building user-centered websites and writing in plain language. However, most did not continue that work. Some of them even got rid of the content that we made for them and pasted their old content back in.
Although they met our goal of moving the websites by the deadline, they found that they had fallen short of setting government agencies up for future success with user-centered websites
Breanne’s story is from a few jobs ago, before security engineering, when she was an SRE with an interest in security. The company saw its first rash of phishing attempts: texts and emails posing as executive staff, asking for sadly normal things: Google Play gift cards and other easily sold gift cards, urging the recipients to please move quickly, because the gift cards were needed now now now.
Breanne and a colleague teamed up to write both a presentation and written training to let people know what these attempts looked like and to establish company norms around communication so that it would be clearer to everyone what legitimate company communication looked like.
The company had fewer than 100 people then, so it made more sense to write a single version of the training that would serve both the engineering department and other staff, including sales and marketing. The distinction here is less to do with who is or isn’t “technical” and whose jobs depend on answering unknown numbers and replying to texts and emails from strangers.
How could two engineers write a workable, concise anti-phishing guide for everyone? How can it go wrong? In our case: not everyone is experienced at writing precise, well-grounded documentation about a complex subject for a varied audience. In our case, they got the job done, but they bumped into some of the limitations of trying to write something about a very specific topic that’s meant to be for everyone.
How can a project’s start doom it?
It’s good to start as you mean to end, which means that thinking of what makes a project like this successful from the start goes a long way toward ensuring its success. So what gets baked into a project plan that can doom it to failure?
Maybe your planning doesn’t entirely account for reality. Maybe your engagement doesn’t account for the real needs limitations and motivations of your users
Or maybe it’s meteor from space or other things outside our control. (This probably felt way less possible before March 2020. Now it’s a pretty good idea to write “large scale crisis” into every risk plan.)
We can’t control everything, but we can control some things. What can we do?
Remember that your partners are users too. Keeping this in mind prevents a lot of issues. Like with end users, it’s worth your time to get to know your internal users’ motivations, limitations, and wants, as well as their hard NOs: things they absolutely will not tolerate.
Seek the similarities. See what behaviors, preferences, and common experiences make groups of users start to cohere in your interactions with them. If your team is having trouble wrapping their heads around this, consider using a lightweight version of personas. Rather than the more involved versions used in marketing and UX, we don’t need to know anyone’s educational level, income, or other demographic information, though it’s not unlikely that some of these divisions will fall neatly between job titles or departments. Instead, look at what’s going to affect your plans:
- What tools are they familiar with? What tools that you’re asking them to use might they not have encountered before?
- Do they work with security a little or often? If they hear from security via a direct message or an email, will their first thought be that they’re in trouble?
- Are they amenable to change or resistant? If they’re resistant, why? (This is a really important question to answer.)
- What motivates them? What’s their definition of professional success?
Avoid stereotypes or unhelpful guesses. Making them too artificial or overly specific is also more likely to harm than help. If it’s just you and a colleague working on this project, it can be plenty to discuss the groups you’re seeing form and plan based on that. However, if you’re doing a longer project or perhaps a larger body of work, you may wish to write them down to share, shape, and reference.
Encountering resistance? Slow down. When you’re starting to roll out your initiative, you may encounter resistance. If the resistance is starting to threaten the velocity or the success of what you’re trying to do, tap the brake and regroup. Form a new hypothesis or think of another strategy—and then seek feedback from the group that wasn’t feeling served before. This is extremely important to do, because we can’t afford to guess in these situations. Fortunately, when you deputize people, they often want to step up and help. If I think someone will be reluctant, I tell them that they hold a key to my success that I can’t under any circumstances produce myself. It’s important to mean this when you say it, but fortunately, it’s completely true, so that shouldn’t be hard.
Make it easy for people to do what you want. Breanne talked about this in her BSides SF talk on documentation last year. Some of the same tactics apply here too: bribery is a legitimate option to overcome some objects. Everyone likes stickers and snacks. However, we can do a little better than that too.
Don’t make users wade through extra reading, video, or other hurdles to do the important thing. Make what you need them to do succinct, clear, and as easy to do as possible. Clear instructions help a lot, as do easy contacts to ask for help. Have the critical stuff up front if you’re asking people to take in information. Executive summaries, a block of text or page or two at the front of a longer document, make sure that busy people have an easier time learning what they need. In longer trainings, the occasional tl;dr block can let people with different attention spans hopscotch through without missing the critical stuff.
This is also a great time to think again of accessibility. (Although it’s always a great time to think about accessibility.) It’s the right thing to do and often legally mandated, but it has one more useful effect, which is that it makes it easier to reach different kinds of learners too. Breanne can hear a video but vastly prefers reading, so a video with transcription reaches those with hearing difficulties as well as those who just like reading, those who can’t turn the sound on, and those who just need to CMD-F or CTRL-F to find the one detail they need to do their job.
This is also a good time for another look back, because history can teach us something. Previous efforts may not be perfect, but they may contain practices and approaches that people are already used to, which means they won’t have to do extra work to learn what you’re doing. It may serve your project well to add additional steps and methods of outreach, but if part of the old approach is getting you a good amount of the way there, it’s likely worth keeping. Security doesn’t have the luxury of perfection a lot of the time, but we can do an 80 percent job in several different ways and achieve something closer to it than we would otherwise.
When you’re asking about the history of projects at your organization, make it clear that you actually want to hear real opinions and that there won’t be retaliation or sore feelings if someone confesses a negative opinion about something that came before.
If all else fails, come back to bribery: security skills look good on resumes, even if the person doesn’t work in security. Try getting people on your side to help them master something important or lucrative. This creates allies.
Okay, but why do we need to think about this at all?
Why do we need to think about this? Aren’t people used to security initiatives and communication around them being subpar or even extremely disruptive? Security is important, and shouldn’t that be enough?
Yes, but—people are part of the system too, and if you’re looking to change the system in an effective and lasting way, you need to work the people part of it too. Both people and the non-people part of systems work better if you give them what they need.
People will not adopt the changes you recommend if you don’t make it easy, explain it well, and make the preferred behavior the easy path. Technical motivations have human implications. It’s just true, and until we reach the robot-controlled singularity, this is just how it’s going to be. We have to adapt.
No matter how brilliant your new security solution, clever process, or other big idea is, it will not work as well as you want it to unless people are on your side. Worse still, you might get a false sense of success as people initially go through the motions of doing what you wanted… only to revert to old habits the next time work gets stressful. We’re looking for something more robust than superficial change.
Once more: how do projects fail?
Projects fail if you don’t get buy-in. This doesn’t need to be unanimous support and a company pep rally celebrating how great your project is. It can be as simple as sending a series of emails ahead of time letting people know what’s coming, when changes will happen, and what they need to do. A little consideration goes a long way.
Projects fail when large, disruptive projects, even ones for the benefit of security, are pushed into being without considering how they affect the people who depend on efficiency or otherwise prefer the previous system for good reason. If people are reluctant, we need to know why and to address that.
Possibly worst of all, projects fail when they’re rotted from the inside by contempt for users and other affected parties by those in power. All of your future efforts will be diminished if the people you’re supposed to be serving can tell you think you’re smarter than them, better than them, or a greater authority on their own lives. People hate this and remember it, and you will face increased friction forever if you get up to this kind of thing. So don’t.
How can we fix this?
Unless you’re Ben Affleck and company, we can’t stop a meteor on a collision course with earth, but there are other levers we can pull to make our projects go smoothly.
Going back to story time: Breanne’s anti-phishing presentation had some things to learn. It couldn’t be too long: people are busy. It needed a short, memorable set of guidelines. It needed to relate causes to effects: “If we don’t present a unified front in not answering phishing texts and looking more carefully at emails, we’ll keep getting hit, and that will have an effect on the business.” It needed to be informed by technical needs but without including too much jargon, because most people who needed anti-phishing guidelines didn’t need to know about how spam emails sneak by Gmail’s spam-targeting AI. Technical curiosity is worth indulging, but it was better as a leave-behind piece for those who want it, leaving the rest of the audience free to go back to their regular work.
Amy’s SF.gov migration is still a work in progress. A lot of their work in 2023 has been around evolving practices and platforms to help their users experience digital transformation. Here are some of their guidelines for that work:
Consider accessibility and cultural differences.
Amy is working on the accessibility of the artifacts she creates and becoming more flexible with the formats and platforms she puts them into. City government is a Microsoft house, and it’s not her team’s preferred set of tools, but many of their users are wary of anything else or simply aren’t allowed to use other products.
Emphasize common ground.
Amy’s background is outside of tech. When she talks with users, she leads with her government background, which allows her to show users their similarities. She makes it a point to visibly not understand things and ask questions, to normalize those behaviors to make others more comfortable.
Say things the easy way.
On SF.gov, they write in plain language, but it can be hard to remember to do that with their users too. If what you need to say is written down, put it into hemingwayapp.com and try to lower the reading level using their suggestions.
Avoid tech jargon and business jargon.
When you need to introduce a technical term, level-set by saying “do you already know the word ____?” Give them a chance to say yes or no, then explain it if they don’t.
Use nonjudgmental language.
Rather than calling something “bad” or another derogatory word, explain the pros and cons. Try to be precise about what you’re pointing out so that you are not expressing judgment. That goes tenfold for anything that your user currently uses or wants.
Speak at a comfortable pace for your audience.
Watch for facial expressions that look worried, like wrinkled foreheads: that could mean people are concentrating hard to keep up with you.
Maintain neutral facial expressions.
Amy does not laugh and does not smile when people ask tech questions. Every question is valid, and every question, especially a very basic or exceptionally strange question, gives you information about what that person needs to know from you.
We sometimes think a smile will be reassuring, but consider that even a reassuring smile can convey “I know the answer and you do not”. As we mentioned earlier, you do not want to give even the appearance of thinking of yourself as smarter than the other person, because that is extremely sensitive and it will be clocked.
Listen actively.
Repeat back what you’re hearing. Paraphrase, but not with tech jargon, because that will sound like you’re correcting them.
Celebrate mastery.
The first time Amy ever felt confident, good, and proud when using a tech tool was in an intermediate Excel class. Amy is not an Excel master, but “confident, good, and proud” is the feeling of mastery. When Amy sees a user experiencing a feeling of mastery, she parties with them, no matter how small a thing it’s for. Amy saw a user feeling mastery because she learned the keyboard shortcut for paste. They celebrated her success as a team, and they’re still a team.
Question your assumptions about your users.
A little humility truly does go a long way. When you don’t understand what your users are doing or why they want what they want, you could try the five whys, because asking why five times can lead you to the real problem.
Example: a tech product that library bought, failed to adopt, and canceled within a year.
- Why did we fail to adopt the product? Staff never made it part of their workflow.
- Why was that? They had trouble training and onboarding everyone.
- Why was that? Rolling out new software to busy front-line staff is very hard, and they did not set aside enough of everyone’s time to make the training stick.
- Why was that? The software wasn’t seen as enough of a priority to take people away from public service.
- And why was that? Well, one person in leadership signed a contract for the software despite every other person saying it wasn’t a good fit for the library.
Answer: lack of buy-in.
Try it out and find a version of it that works for you. Sometimes it’s a good tool to use when you find yourself feeling annoyed by the users you’re meant to be serving.
Ask like a librarian: use reference interviews.
Amy was a librarian for 17 years and wants to teach you about reference interviews. When you go to a library and say can you help me find a book, that is the beginning of your reference interview. In this interaction, a trained librarian is assessing:
- The words you chose
- Whether there was hesitation in your voice
- Your body language
- Tone
- The way you approached them
- What else you are holding in your hands
- And more
A secret of reference interviews: the cover isn’t blue. Amy has been surprised, in the tech world, by how literally people take requests from users. There’s a librarian adage about “the book with the blue cover.” Asking for things inaccurately is expected behavior. Not because people are lying or not smart, but because this is the way human brains work: imprecisely.
A good reference interview helps a person form their question. Try tangential lines of questioning. When you’re looking for the book with the blue cover, it’s tempting to keep asking about the cover. Is there a picture? Light blue or dark blue?
Don’t bother. The cover is irrelevant.
Ask questions about something else. When did you read the book? In the 70s? Last year? Was it a book you were assigned in school? Did you get it at a Scholastic book fair? Was the main character an animal or a person? Amy uses a mix of broad and specific questions to try to snag on some detail that triggers a new, meaningful memory. The same technique can work for zeroing in on product requirements.
Learn user vocabulary and motivations.
Every question is valid. A question might sound silly to you, but it is not silly to the person asking. If you are a knowledge authority figure, chances are they had to screw up their courage to ask you.
Keep a neutral facial expression.
We won’t tell you not to smile, but remember that a smile can read as condescending.
Get to know their vocabulary, and use it.
People often adapt their language in ways they assume make sense to us when they ask questions. They use vocabulary they’ve heard people in our position use. They focus on a detail that’s related to what they want because they associate that detail with techy people.
A common example of this in tech is a user who insists on a particular feature, but has an inaccurate understanding of what it does. They know what outcome they want, but ask for a thing that won’t get them that outcome. Why? Because they are trying to communicate the outcome to you in what they assume is your language. Repeating what users said and paraphrasing, in addition to being good active listening, gives them a chance to edit and refine their ask. Listen to the vocabulary your partners use and use it too.
Be wary of contempt.
If you work with anyone who expresses contempt for your user, be very wary of them. All users are beautiful, but some are harder to reach. If you don’t like working with users and find yourself disdainful of their needs, consider that in your career path. You have more than one kind of user and they are all important.
Tie directives to outcomes your users value.
They may not be the same outcomes you value! Find common fears and desires among the users you’re meant to serve and appeal to them, ideally leaning more on the desires than the fears. It’s better to only reference the scarier things (“If we don’t complete this initiative, we’ll have our government certification pulled, and we will all be unemployed”) only with people who know you well. Instead, try invoking more immediate stakes. Breanne likes “I don’t want you to get a phone call at 3 AM if something goes wrong, because everyone understands that.
Takeaways
- Work to understand actual motivations behind resistance.
- Learn to speak the user’s language: vocabulary, accessibility, and technological knowledge.
- No dictates without relating them to your user’s actual needs and priorities.
- Try reference interview secrets to understand the bigger picture.
- Helping people to master something important/lucrative will get them on your side.
