Keeping Up With the CEO: 20 Tricks and Tools

I find it fascinating to learn about all of the different techniques and tools my peers and clients use to achieve the same basic tasks that I do. In order to feed my curiosity and kick start a conversation about our personal “stack” of apps I’ve shared 15 of my favorite tools, five productivity tricks, as well as half a dozen things I know I could be doing better. Hopefully you can find something new to help your day-to-day, and I look forward to your feedback in the comments below!

– Jesse Lakes (CEO / Co-Founder)

Time Management: Rescue Time

Let me first dive into (Tool #1) RescueTime in order to help guide the conversation. This was a Tim Ferriss / 4-Hour Workweek recommendation and is a handy (freemium) menu bar-based app that watches all of the apps and websites you use in order to give you insight into what it is that you spend your day doing. You can also use it to limit your access to some apps / sites if you are a known procrastinator and need the help.

The dashboard is always available but the weekly emails are what I find most interesting and force a weekly review of my habits.

RescueTime monthly review

RescueTime Monthly Dashboard

As you’ll notice January was a busy month for me (and an awesome month for the company). We came out of the holiday break fired up for the new year and it’s obvious from the graph. The other obvious piece, and I’ll call myself out throughout this doc, is that (Fail #1) I only had two days where I completely stepped away from my computer – there should be no excuse for not doing this more. I’m a firm believer that you need to step away to recharge so that your time working is more productive. I also believe that as a CEO a good percentage of my job should be talking to people in person, not through an app.

Communication & Scheduling

Breakdown of my "Communication & Scheduling" time.

Breakdown of my “Communication & Scheduling” time.

Email: Apple Mail

My life mostly revolves around my inbox. While I’m happy to finally be achieving a good balance of proactive vs. reactive work, the Apple Mail app is essential to both.

We use Google Apps to manage our mail and calendar and while it does work, I’m not in love with the system and am often annoyed that it can take 20-30 minutes some mornings for my mail to finish syncing.  I do, however, love the ability to (Trick #1) set up rules and filters that apply to my inbox no matter what device I’m using to check my email.

I’m also slowly catching on to using mail tracking plugins to help with prospecting and tracking important emails. At a high level these plugins will alert you when an email you sent is opened, from what country it was opened, what device did so and sometimes if the links you included where clicked or attachments read. I started with (Tool #2) YesWare after one of my Biz Dev guys gave it a glowing review. While it was solid tool, it only worked in Chrome when I was using Gmail (again my preference is the Apple Mail app) so I rarely used it. Once we drank the Kool-Aid with using HubSpot I’ve since taken a liking to (Tool #3) SideKick. While I don’t think SideKick is anywhere near as full featured as YesWare they have an Apple Mail plugin so I can more easily use it when I need it (I can have it set by default NOT to track emails).

Besides always trying to be timely with replies to incoming inquiries, I use Mail to take and send myself notes, outline ideas, and keep a list of my To Do items. Fail #2 – Should I be using a specific To Do list app? Would something like Evernote or OneNote be better for this?

Messaging: HipChat, Skype, Join.Me

Hipchat

As a team we fell in love with Atlassian early on and while I’m not a dev and can’t appreciate some of their more technical tools I like their wiki software and especially (Tool #4) HipChat. We use HipChat as the team’s main messaging client where it works flawlessly (yes, I’ve heard great things about Slack too). I’m a big fan of the seamless ability to paste images directly into the client and then get a secure URL for that image that I can use elsewhere.

I’m also a fan of how easy it is to integrate bots into HipChat and my favorite is one we set up so that the team can see when credit cards are added (Trick #2 – we do this by leveraging Papertrail but Zapier can also help here). It’s a quick “win” that we can all quickly smile about and constantly reminds us that people are happy to pay for what we have built.

Skype

I’m a long time user of (Tool #5) Skype and still prefer it over HipChat and Google Hangouts for voice and video calls. I pay the small yearly premium so we can get multiple members on video. In the early days we did all of our client meetings over Skype due to the international aspect of our business and its global user base. I also like the fair prices for international phone calls and the $25 I put into credits have lasted me for years.

With Skype I also use the (Tool #6) “Call Recorder for Skype” plugin to easily capture audio and video.

Join.me

While I didn’t initially like (Tool #7) Join.Me I’ve found that it’s much more “professional” for hosting (potential) client conversations. It’s kind of a pain that they require new users to download a plugin for doing VOIP audio but now that it’s picking up popularity it’s becoming less of an issue. I also like that you can use it as an international conference calling line without needing the screenshare piece. Audio / video quality is also more consistent.

Scheduling: Calendar

I’ll come straight out and say that this is an obvious Fail #3 – not using a better calendar. Because time is so important and I’m tied to my calendar I should really have moved past the default app (while it is decent) and invested sometime ago and started using Fantastical 2! I’ve only ever heard that it’s awesome. What do you think?

Design & Composition

RescueTime's report of my "Design & Composition" usage.

RescueTime’s report of my “Design & Composition” usage.

Presentations: Keynote, Preview

I love (Tool #8) Keynote! Early in my career at Apple our whole marketing team took a class on Keynote put on by the infamous Ryan Spratt. It was an eye opener on how powerful this tool was and quickly became a favorite. When we do a client demo we will often customize a deck for them and this is done through Keynote. While Mail is great for me to “doodle” with words, Keynote is my app of choice to “doodle” with thoughts that require images.

While I love to build with Keynote I rarely use it for presenting instead opting for Preview, the built in PDF viewer. It’s a very lightweight app but works well. The tools to quickly edit and digitally sign a PDF are icing on the cake (Trick #3).

Composition: Google Docs

Google Docs. Period. It’s too easy to share and work collaboratively on items. However, I’ll call myself out here in that (Fail #4) I’ve never investigated any additional plugins to help increase productivity here. What do you use so that your team gets even more value from the Google Docs suite of apps?

Business

RT-Business

RescueTime’s listing of my top Business app usage.

Spreadsheets: Excel, Google Sheets

I may have a bit of an obsession with spreadsheets. I honestly love playing with numbers and seeing what kind of information I can squeeze out of row after row of data.

Excel is my tool of choice for making up in my ignorance of SQL or when the size of the data set gets exciting. I’m also a fanatic about keyboard shortcuts and really like Ash Roy’s Productivity Insights (Trick #4) list of the top keyboard shortcuts for Excel.

While Excel is my tool of choice for number crunching I use Google Spreadsheets for tracking whatever I need to track (marketing metrics) or collaborative projects (account management projects).

Team Moral: TinyPulse

(Tool #9) TinyPulse is a great app that lets you keep an eye on team morale and retention. This awesome service sends a weekly question to your team where they can anonymously answer it each week, provide general feedback and give “cheers” to other team mates. We go through the results during our weekly stand up and it’s been super insightful for picking up on concerns before they become full blown issues.

Inbound Marketing: HubSpot

We dove into the “marketing automation” realm last summer after getting absolutely frustrated with the Zoho CRM and after reviewing Infusionsoft, Pardot, Marketo, and PipelineDeals we went with (Tool #10) HubSpot. We’ve learned a lot in the process of getting it integrated and it’s obvious we have a lot more to learn, but it’s replaced Moz, Zoho, and Google Analytics (at least for me). The one disappointment is that their CRM wasn’t as fully developed as we would have liked…

Banking: Chase, Silicon Valley Bank

From the screenshot you can also see that Chase is our bank (for no real reason other than our account rep is super nice, they have a convenient location near my house, and it’s also my personal bank). However, I’m not a fan of their fees and the challenges of depositing international paper checks (not their fault) but after learning more about Silicon Valley Bank I’ll put my Fail #5 as not taking full advantage of their plan for startups.

Utilities & Other

These are the tools I thought were important to include even though they don’t show up high on my RescueTime report.

Intelligence: Ghostery, BuiltWith, RedirectDetective, Charles, Mention

Similar to why I’m writing this article, I tend to be a bit curious about how things work (for example, a recent blog I wrote: What Can You Learn From A Short URL?). Here are a few tools / sites that help me poke around.

The (Tool #11) Ghostery plugin is awesome for getting a quick overview of the tools used to build a site or understand how they do their marketing.

The online tool (Tool #12) BuiltWith does a similar thing but goes deeper into the technical details and gives more of a “full stack” perspective.

In my world understanding how a link resolves is important and I use the site Redirect Detective (Tool #13) to get a quick overview or test and then Charles Web Proxy (Tool #14) if I have to dive deep.

And one of my all time favorites to wrap things up. Mention (Tool #15) is an amazing tool to keep an eye on keywords, competitors, and your brand across the web. Similar to Google Alerts, Mention keeps an eye on the web and lets you know when something interesting is being said. While not shown above I use this tool everyday to stay on top of the industry.

Finder: Keyboard Shortcuts

As I mentioned earlier I’m a big fan of keyboard shortcuts and this is guide (Trick #5) from Product Insights has all of the good ones – 45 Insanely Useful Mac Keyboard Shortcuts.

What’s the best tool for pulling up specific apps, doing basic math, or searching for a doc, preferably without having to use the mouse? There has got to be a better app than using Spotlight (Cmd + Space) (Fail #6).

What do you think?

What is your favorite tool or trick? Did you catch any of my other fails? Thanks for reading and I look forward to your feedback!