Lessons learned from running a web development agency. Tips on hiring, firing, management, marketing, sales and creating new habits.

1. Well, that
didn’t
work.
Jason Siffring
@siffring

2. Treat your business like a
science experiment.
• Hiring (and firing)
• Managing a (Remote) Team
• Sales & Marketing

3. • 8 year old web development studio
• Based in Chicago
• 7 employees + 4 contractors
• Completely remote team

4. Hiring
(Always be doing it.)

5. Does this sound familiar?
• Your new contractor started off strong, but has
missed every deadline.
• They over promise and under-deliver.
• When the going gets tough, they go silent.
• They stop returning phone calls.

6. I can’t find good people!

7. If you start looking for
help when you need it,
you waited too long.

8. You had me at Trello

9. Your first hire

11. Your first fire

12. People don’t change
(Generally)

13. Take Action
➡ Start a Trello board, Google Doc, etc. to track
potential hires
➡ Brainstorm three people you might like to work
with
➡ Schedule coffee, lunch or phone call with one of
them “just to catch up”

14. Hiring Resources
• Trello board we use for hiring
• Trello board we use for on-boarding

15. Managing a (remote) team

17. Force communication
that would happen
naturally in an office

18. How do you know if
they’re working?

20. Daily Virtual Standup

21. 1:1

22. Weekly Pair Meetings
(This is our hallway conversation.)

23. Monthly Show & Tell

24. Delegation is easier
with documentation

25. You’re already delegating!
• Amazon Subscribe-n-Save
• Photoshop Macros
• Scripts and reusable code libraries
• DRY code

26. What works for 3 people
doesn’t always work
for 5, 10, etc.

27. Take Action
➡ Schedule a monthly 1:1 meeting with each of
your team members
➡ Put it in the calendar!
➡ Identify one thing you’re spending time on that
you can train someone else to do

28. Management Resources
• “What to Expect when You Start Having 1 on 1s
with Your Team”
• “The 12 Week Year” -Brian Moran
• Surprise Highway Playbook
• Thoughtbot Playbook
• Zirtual - US based virtual assistants

29. Sales
(Always be doing it)

30. We don’t have enough work!
Sell, sell, sell
We have too much work!
Work, work, work
Repeat

31. 20 emails
6 meetings
1 client
$120,484

32. Use a CRM
• Spreadsheet
• Highrise
• Trello
• Contactually
• Pipedrive
• Close.io

33. Follow up!

34. –The Magic Email by Kurt Elster
“Since I have not heard from you on this, I have
to assume your priorities have changed.”

35. Recurring Revenue is Magic

36. Recurring Revenue is Magic

37. Recurring Revenue is Magic
surprisehighway.com/website-maintenance

38. Take Action
➡ Block out 1 hour in your calendar
every week for sales.
➡ Early in the week. Early in the day.
➡ surprisehighway.com/website-maintenance

39. Sales Resources
• “Million Dollar Consulting” -Alan Weiss
• Boomerang for Gmail
• Productize course -Brian Casel
• 30x500 course -Amy Hoy
• Wheelhouse productized services directory

40. Marketing
(Always be doing it.)

41. Take your own advice

42. windy.io

43. Outsource your weakness
Content Creation
philipmorganconsulting.com
Design
shapingthepage.com
Development
(cough) surprisehighway.com (cough)

44. Marketing Resources
• “The Positioning Manual” -Philip Morgan
• Drip simple marketing automation

45. Let’s get real

49. You have all the skills you
need to be successful.

50. You “just” need to
change your habits.

51. Surprise!
(This talk is really about habits.)

52. Three things can change
behavior in the long term:
1. Have an epiphany
2. Change your environment
3. Take baby steps
–BJ Fogg, Stanford PhD
tinyhabits.com

53. How to Form Tiny Habits
• Pick something you do frequently
• Identify a trigger
• Reward yourself

54. My New Habits
When my feet hit the floor first thing in the morning…
I tell myself, “Today is going to be a good day.”
After I brush my teeth…
I floss one tooth.
When I sit down at my desk in the morning…
I identify one thing I need to get done that day.

55. Accountability

56. Take Action
➡ Choose one thing you’re going to do differently
next week to improve your business
➡ Tweet, email or text me your one thing
➡ I will follow up on Friday to see if you did it.

57. @siffring jason@surprisehighway.com (415) 305-1992
surprisehighway.com/peers