How do dividend policy, debt issuance, share issuance and CEO managerial skills affect corporate tax planning or tax avoidance? In my first essay, I investigate how dividend payout is related to proxies for tax avoidance, including cash effective tax rates (CASH-ETR) and book-tax differences (BTD). Dividend policy may lead to tax avoidance because dividends represent relatively fixed commitments to transfer cash to shareholders. I find that dividend payout is negatively related to CASH-ETR and positively related to BTD, indicating that dividend payout is associated with a tax avoidance strategy. In the second essay, I examine whether firms’ issuance of equity and debt securities are associated with cash savings through tax planning. I find that an increase in share issuance is associated with a decrease in cash effective tax rate (CASH-ETR), suggesting that firms that issue shares save cash by tax planning. I do not find any evidence that debt issuance reduces CASH-ETR or induce tax avoidance behavior. In the third essay, I study the relation between tax avoidance and general managerial skills acquired by CEOs through their lifetime work experience. Managerial skills are two types: general managerial skills which are transferable across firms and industries and specific managerial skills, which are valuable only to a specific firm or industry. Using OLS regression on a sample of S&P 1500 firms for 1993-2007 period, I find that CEOs with general managerial skills (generalist CEOs) tend to engage more in tax avoidance strategy compared to CEOs with specific managerial skills (specialist CEOs). This evidence implies that CEO managerial skills matter for corporate tax planning.