Somtimes I forget to open Outlook in the morning, this helps as a cron task

ensure-outlook.bash

#!/usr/bin/env bash
# vim: set syntax=sh

ps aux | grep -v "grep" | grep "Microsoft Outlook" > /dev/null
outlook_ret=$?
day=`date +%u`

# Make sure it's a weekday and Outlook is running
if [ "$day" -ge 1 -a "$day" -le 5 -a "$outlook_ret" -gt 0 ]; then
  osascript -e 'display notification "Please start Outlook" with title "Nag Bot"'
fi

Only runs on a Mac with gdate